My 3-Week New York State Road Trip (Scenic Getaways)

by Jon Miksis
3-Week New York State Road Trip Itinerary
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Having road-tripped all over the Northeast, I can confidently say that New York State is one of the most underrated gems in the U.S. Beyond the skyscrapers of NYC, you’ll find mountain ranges, wine trails, historic small towns, and more natural beauty than most people expect. Over the years, I’ve pieced together my ultimate route, and this guide pulls it all into one epic road trip itinerary.

The ultimate 3-week New York State road trip itinerary

Making the Most Incredible New York State Road Trip

If you have three weeks, you can really soak it all in – from the Hudson Valley and Catskills to the Adirondacks, Finger Lakes, and Niagara Falls. That’s my recommended sweet spot. But if you’re short on time, don’t worry. You can absolutely condense this into two weeks, or even focus on one region (like the Finger Lakes or the Adirondacks) if you only have a week. Personally, I love breaking New York into chunks so I have an excuse to keep coming back year after year.

One thing to know: New York is bigger than most people realize. Driving from NYC to Niagara Falls can take 7–8 hours without stops, so pacing yourself is key. That’s why I’ve structured this itinerary to balance city time with nature, and long drives with shorter days full of experiences. Trust me, it makes the trip so much more enjoyable.

Below you’ll find my 21-day New York State itinerary, complete with a map, daily highlights, and insider tips from my own trips. Whether you follow it exactly or just use it for inspiration, you’ll get an amazing taste of what the Empire State has to offer.

Me standing next to waterfall in the Finger Lakes
Get ready to see all my favorite spots in Upstate NY!

Road Trip Itinerary Map for New York State

Here’s a handy map highlighting all the must-see stops for my New York State road trip. I’ll break down each destination below and share tips to make your journey smooth and super enjoyable.

Days 1-2: New York City

There’s no better place to kick off your New York State road trip than the Big Apple itself. New York City is a whirlwind of energy, culture, and iconic sights. Every time I visit, I find something new, but the classics never disappoint. From world-famous landmarks to hidden neighborhood gems, NYC is the kind of place that rewards both first-timers and repeat visitors.

Here’s how I’d recommend spending your first two days:

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Day 1: Iconic Landmarks and Culture

  • Times Square: Start your trip in the heart of Manhattan. Times Square can feel chaotic, but the energy is contagious — especially after dark when the lights glow brightest. Pro tip: go early in the morning if you want fewer crowds and better photos.
  • Central Park: Just a short walk from Times Square, Central Park is the perfect escape from the bustle. Rent a bike, row a boat, or simply wander through the winding paths. Spring blossoms and fall foliage here are absolutely magical.
  • The Metropolitan Museum of Art (The Met): One of the greatest museums in the world. Even if you’re not a huge museum person, the rooftop garden alone is worth a visit for its skyline views.
  • Broadway Show: There’s nothing like seeing a Broadway performance in NYC. I’ve scored same-day tickets from the TKTS booth in Times Square, which is a great way to catch a show without breaking the bank.

Day 2: History and Neighborhoods

  • Statue of Liberty & Ellis Island: Take the ferry from Battery Park for one of the most iconic experiences in the U.S. Seeing Lady Liberty up close and exploring the Ellis Island museum is a powerful way to connect with American history.
  • 9/11 Memorial & Museum: A moving and important stop. The reflecting pools are beautiful in their simplicity, and the museum is incredibly well done.
  • Wall Street & the Financial District: Take a quick stroll through the canyons of finance. Don’t forget to stop by the Charging Bull statue — I’ve seen people line up just for a quick photo here.
  • Chinatown & Little Italy: These neighborhoods are perfect for a food crawl. Grab dim sum in Chinatown, then walk a few blocks north for a cannoli in Little Italy. One of my favorite combos on any NYC trip.

If you’re planning to hit multiple big attractions (The Met, MoMA, Empire State Building, Top of the Rock, etc.), consider a CityPASS to save money. Book Statue of Liberty tickets and Broadway shows in advance if you’re visiting during summer or the holidays. Things sell out fast.

If you have time: explore the neighborhood of Queens, which has an amazing foodie scene and scenic views of the waterfront.

Begin your New York road trip in NYC, exploring iconic landmarks and experiencing the city’s vibrant energy.
Begin your New York road trip in NYC, exploring iconic landmarks and experiencing the city’s vibrant energy.

Days 3-4: Hudson Valley

After the non-stop buzz of NYC, the Hudson Valley feels like a deep breath of fresh air. Just a couple hours north of Manhattan, this region is known for its river views, charming small towns, art museums, and outdoor adventures. I’ve done this drive in every season, and honestly, it’s hard to pick a favorite — fall foliage is unreal, but spring blossoms and summer sunsets over the Hudson are just as beautiful.

Here are some highlights I recommend for your two days in the valley:

Top Attractions in the Hudson Valley

  • Sleepy Hollow: Famous from Washington Irving’s Legend of Sleepy Hollow, this town leans into its spooky charm. The Sleepy Hollow Cemetery is worth a visit (especially around Halloween), and the riverside trails are surprisingly peaceful. I went in October once, and the whole town was decked out in pumpkins and lanterns – this is one of the most livable areas of Hudson Valley for sure.
  • Kykuit, the Rockefeller Estate: A stunning estate once home to the Rockefeller family. The gardens, art collection, and views of the Hudson River are incredible. Tours do sell out, so book ahead if you can.
  • Storm King Art Center: This massive outdoor sculpture park is one of my favorite spots in all of New York. Walking through rolling hills dotted with larger-than-life sculptures is both surreal and relaxing. Pack a picnic and spend a few hours here.
  • Mohonk Preserve: If you’re craving a hike, this is the place. Trails range from easy walks to adventurous scrambles. The Labyrinth and Lemon Squeeze trail is a challenge, but the payoff views are unforgettable.
  • Dia:Beacon: A modern art museum inside a former Nabisco factory. It’s huge, minimalist, and perfect for anyone who loves large-scale installations.

More Things to Do

  • Walkway Over the Hudson: A pedestrian bridge that gives you sweeping views from 200 feet above the river. I walked this at sunset once, and the colors reflecting on the water were unbelievable.
  • Hudson River Cruises: Scenic boat rides are a fun way to take in the valley from a different perspective. Fall cruises for leaf-peeping are especially popular.
  • Culinary Institute of America (CIA) in Hyde Park: If you’re a foodie, dining here is a must. The student-run restaurants are surprisingly affordable for the quality, and every meal I’ve had here has been memorable.
The Hudson Valley offers scenic beauty, perfect for unwinding after the hustle of New York City.
The Hudson Valley offers scenic beauty, perfect for unwinding after the hustle of New York City.

Days 5-6: Catskills

From the Hudson Valley, it’s just a short drive west into the Catskills, one of my favorite regions in New York for nature, small towns, and laid-back vibes. The Catskills have this nostalgic feel (they were a major vacation destination in the mid-20th century), but today they’ve reinvented themselves as a mix of outdoor adventure and hip, artsy communities.

I love coming here in the fall…the foliage is outrageous! But winter snowshoeing, spring waterfalls, and summer tubing on the creeks are just as magical. Two days is a nice amount of time to hit the highlights and still soak up the mountain atmosphere.

Top Attractions in the Catskills

  • Kaaterskill Falls: One of the tallest waterfalls in New York, dropping 260 feet in two tiers. The hike is fairly short but steep, and the spray at the base is refreshing in the summer. I still remember the first time I rounded the bend and saw the full cascade — it’s breathtaking.
  • Hunter Mountain: A year-round adventure hub. In winter, it’s ski slopes and snowboarding; in summer, you can hike or take the Skyride chairlift for sweeping views. If you’re up for a thrill, ziplining here is incredible.
  • Woodstock: This artsy town is famous for its name (even though the 1969 music festival happened in Bethel, not here). Woodstock has a great mix of galleries, boutique shops, and cozy cafes. It’s the kind of place where I always end up buying a quirky piece of local art.
  • Phoenicia: Small but super charming. In summer, tubing down Esopus Creek is a must-do — it’s relaxing, a little silly, and the perfect way to cool off on a hot day.

More Spots to Explore

  • Catskill Park: Nearly 700,000 acres of protected wilderness. If you’re into hiking, check out Giant Ledge and Panther Mountain for sweeping ridge views.
  • pus 40: A mind-blowing sculpture park in Saugerties built almost entirely out of stone by one artist over decades. It’s like walking through an outdoor labyrinth.
  • Bethel Woods Center for the Arts: The actual site of the 1969 Woodstock Festival. Today, it’s a museum and live music venue — summer concerts here are a blast.
  • Sullivan Catskills Dove Trail: A fun scavenger-hunt-style trail featuring dozens of painted dove sculptures spread across the region, commemorating Woodstock’s 50th anniversary.

I recommend visiting midweek if you can…weekends bring lots of NYC crowds. Food-wise, don’t miss the region’s farm-to-table restaurants – I’ve had some of my favorite meals in tiny towns here.

The Catskills, with forests, waterfalls, and charming towns, are perfect for nature lovers and fall foliage.
The Catskills, with forests, waterfalls, and charming towns, are perfect for nature lovers and fall foliage.

Days 7-8: Albany and Saratoga Springs

After the mountain air of the Catskills, head north for a mix of history, culture, and small-town charm. Albany, New York’s capital, has grand architecture and museums, making it one of the top places to live and visit in New York. Saratoga Springs is all about mineral baths, horse racing, and an artsy, lively downtown. Spending two days here lets you balance city exploring with a touch of relaxation.

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Albany Highlights

  • New York State Capitol: Albany’s most impressive building by far. The guided tours are excellent and give you a sense of the politics and history that shaped New York.
  • Empire State Plaza: A striking mix of government buildings, art, and open space. In the winter, they even set up ice skating here.
  • New York State Museum: I’ve spent hours here — it’s packed with exhibits on everything from New York’s geology to the 9/11 attacks. Perfect for a rainy day.
  • Washington Park: Designed by the same folks behind Central Park, it’s a beautiful place for a stroll. If you’re here in May, the Tulip Festival is gorgeous.

Saratoga Springs Highlights

  • Saratoga Spa State Park: Relax in the mineral baths (I did this after a long day of driving — heaven), explore the trails, and catch a concert at Saratoga Performing Arts Center (SPAC).
  • Saratoga Race Course: If you’re visiting in late July through early September, don’t miss the thrill of live horse racing. Even if you don’t bet, the atmosphere is electric.
  • Congress Park: A peaceful spot in town with mineral springs and a charming historic carousel.
  • Downtown Saratoga: Boutique shops, cozy cafes, and farm-to-table dining. I recommend grabbing coffee at Uncommon Grounds and people-watching along Broadway.
  • Yaddo Gardens: A hidden gem just outside downtown — serene gardens perfect for a quiet morning walk.

Extra Stops If You Have Time

  • Hudson River Cruises (Albany or Troy): Scenic boat tours that show off the valley from the water.
  • Albany Institute of History & Art: A small but fascinating museum with Hudson River School paintings and regional history.
  • Saratoga Winery: If you’re a wine lover, this is a fun, low-key spot to sip local varieties.
Saratoga Springs is known for its mineral springs, vibrant arts scene, and historic horse racing track.
Saratoga Springs is known for its mineral springs, vibrant arts scene, and historic horse racing track.

Day 9: Lake George

When I first visited Lake George, I instantly understood why it’s called the “Queen of American Lakes.” The water is unbelievably clear, the surrounding mountains are gorgeous, and the little lakeside village feels like a classic summer getaway. You could easily spend an entire week here, but even with one day, you’ll get a great taste of what makes this place special.

Top Things to Do in Lake George

  • Fort William Henry: I loved learning about the French and Indian War here — the musket-firing demo was a highlight. If you’re into history, this stop really brings the past to life.
  • Lake George Steamboat Company: Cruising the lake on a historic steamboat was one of my favorite memories from the trip. You get the best views of the mountains and the stately summer homes along the shoreline.
  • Prospect Mountain: I drove to the summit on my last trip, and the panoramic views of the Adirondacks blew me away. On a clear day, you can see into Vermont.
  • Million Dollar Beach: After all the sightseeing, I spent an afternoon relaxing here. It’s great for swimming, picnicking, or just watching the boats go by.

More Attractions & Activities

  • Adirondack Extreme Adventure Course: I tried one of the zip-lines here — definitely a thrill if you like a little adventure between your more relaxed lake time.
  • Shelving Rock Falls: A quieter hike I did on the east side of the lake. The trail isn’t difficult, and the waterfall is really pretty.
  • Lake George Village: It’s touristy, but I had fun wandering the shops and grabbing a bite at a casual lakeside spot.

Where to Stay

Lake George, the "Queen of American Lakes," offers clear waters, scenic views, and rich history.
Lake George, the “Queen of American Lakes,” offers clear waters, scenic views, and rich history.

Days 10-11: The Adirondacks (Lake Placid)

Lake Placid is one of those places I keep going back to. It’s beautiful year-round, and every season has its own vibe…summer hikes, blazing fall foliage, winter skiing, and spring waterfalls roaring with snowmelt. I love how it feels both peaceful and adventurous at the same time.

My Favorite Things to Do in Lake Placid

  • Mirror Lake: Walking the 2.7-mile loop around Mirror Lake is always the first thing I do when I arrive. It’s peaceful, and the views of the mountains reflecting off the water are incredible. In winter, I skated across the frozen lake, which felt surreal.
  • Olympic Sites: I geeked out visiting the Olympic Jumping Complex. Taking the chairlift up to the top of the ski jumps gave me such an appreciation for the athletes. The Olympic Center downtown also has a great museum if you’re into sports history.
  • Whiteface Mountain: I’ve driven the Veterans’ Memorial Highway up to the summit, and honestly, it was one of the best views I’ve ever had in New York. In the winter, I snowboarded here — it’s challenging but amazing.
  • High Falls Gorge: I went in the fall, and the leaves made the waterfalls even more dramatic. The trails are easy and well-maintained, so it’s perfect for a quick stop.

More Adirondack Adventures

  • Hiking Mount Jo: This short hike is my go-to recommendation. It’s only about 2 miles roundtrip, but the summit view of Heart Lake and the High Peaks is ridiculously good for the effort.
  • Cascade Mountain: If you’re ready for more of a challenge, Cascade was my first “High Peak,” and it’s a great intro to Adirondack hiking.
  • Saranac Lake: I love this artsy little town nearby. I grabbed coffee at a local café and strolled the waterfront — it’s less touristy than Lake Placid but still super charming.
  • Adirondack Wildlife Refuge: On one trip I visited the refuge and got to see wolves and eagles up close. It’s a great family-friendly stop.

Wondering where to stay? I highly recommend Golden Arrow Lakeside Resort, right on Mirror Lake. I stayed here once in the fall, and waking up to the fog lifting off the water was magical.

Lake Placid, in the Adirondacks, is known for its natural beauty, Winter Olympics history, and year-round outdoor activities.
Lake Placid, in the Adirondacks, is known for its natural beauty, Winter Olympics history, and year-round outdoor activities.

Days 12-13: Thousand Islands

The first time I went to the Thousand Islands, I was blown away. I knew it was going to be pretty, but I didn’t expect over 1,800 little islands, some of the coolest islands in New York. Cruising along the St. Lawrence River feels almost surreal, with castles, lighthouses, and cottages dotting the water. It’s one of those places where you just have to slow down and soak it all in.

My Favorite Things to Do in the Thousand Islands

  • Boldt Castle: This was hands-down my favorite stop. The story behind it (a millionaire building it for his wife, who tragically passed before it was finished) makes it bittersweet, but wandering through the restored rooms and gardens on Heart Island was magical. The boat ride there also gives you fantastic views.
  • Singer Castle: If you’re into secrets and passageways, this place is a dream. Touring Dark Island and hearing the guides explain how the family once lived here felt like stepping back in time.
  • Boat Tours: I did a sunset cruise one evening, and it was incredible – the islands glowing in the golden light, the river calm and peaceful. If you only do one thing here, make it a boat tour.
  • Thousand Islands Bridge: Driving across the bridges was such a cool perspective. I pulled over at one of the overlooks and just stared at the islands below. It’s also a fun way to pop into Canada if you have your passport.
  • Clayton: I loved this little riverside village. The Antique Boat Museum surprised me – I’m not even a big boat person, but the craftsmanship was jaw-dropping. Plus, the shops and restaurants along the waterfront are perfect for a relaxed afternoon.

More Things I Recommend

  • Alexandria Bay: This is a lively town right on the water. I had dinner on a patio overlooking the river, and it was one of those pinch-me moments. Great place to base yourself.
  • Wellesley Island State Park: I camped here one night, and waking up with the sunrise over the river was unreal. They also have the The Minna Anthony Common Nature Center, which is awesome for hiking and spotting wildlife.
  • Rock Island Lighthouse: I took a little side trip here and climbed the tower. The view of the river from the top was stunning…definitely worth the effort.

The Thousand Islands are best explored in late spring through early fall. I went in October once, and the fall foliage mixed with the islands was breathtaking. Some of my favorite NY Airbnbs are here!

Boldt Castle on Heart Island is a stunning, unfinished mansion with a tragic love story.
Boldt Castle on Heart Island is a stunning, unfinished mansion with a tragic love story.

Day 14: Rochester

Rochester was such a pleasant surprise for me. I originally thought of it as just another upstate city, but once I got there, I realized it has this really cool mix of history, art, and natural beauty. Sitting right on Lake Ontario, it feels both urban and outdoorsy at the same time.

My Favorite Things to Do in Rochester

  • The Strong Museum of Play: This was easily the highlight of my visit. Even as an adult, I had a blast wandering through the exhibits and seeing the National Toy Hall of Fame. I spent hours here — it’s interactive, nostalgic, and so much fun.
  • Highland Park: I timed one of my trips with the annual Lilac Festival, and wow, the colors and smells were unreal. Even outside of May, it’s a peaceful place to walk with rolling hills and gardens designed by Frederick Law Olmsted (the same guy behind Central Park in NYC).
  • George Eastman Museum: As someone who loves photography, this was a must. Exploring the mansion of Kodak’s founder while learning about the history of film was fascinating. The gardens outside were stunning too.
  • Susan B. Anthony Museum & House: Walking through the home of such an important figure in American history gave me goosebumps. The guides did a fantastic job of bringing her story to life.
  • Seabreeze Amusement Park: I went here in the summer, and it had such a classic, nostalgic feel. The rides overlook Lake Ontario, which makes for some awesome views.

Other Spots I Recommend

  • Genesee Riverway Trail: I biked a section of this trail, and the view of High Falls cutting right through the city was incredible. It’s one of the best urban waterfalls I’ve ever seen.
  • Ontario Beach Park: Spending a lazy afternoon here by Lake Ontario was the perfect reset during my road trip. The vintage carousel is a charming bonus.
  • Rochester Public Market: I love local food markets, and this one was packed with vendors selling everything from fresh produce to international street food.
  • Mount Hope Cemetery: Not only is it historic (Susan B. Anthony and Frederick Douglass are buried here), but it’s also a beautiful, peaceful place to walk around.

Rochester surprised me with its food scene too. I tried the famous “Garbage Plate” at Nick Tahou Hots…it’s messy but definitely a rite of passage. On another night, I hit up the Genesee Brew House for local craft beer and an awesome rooftop view of the river.

The Genesee Riverway Trail offers scenic views along the river, especially near High Falls.
The Genesee Riverway Trail offers scenic views along the river, especially near High Falls.

Days 15-17: Finger Lakes

Every time I road trip through New York, the Finger Lakes region ends up being one of my favorite stops. I honestly think it’s one of the most underrated regions in the U.S. With its dramatic waterfalls, rolling vineyards, and charming little towns, it feels like a mix of Tuscany and a national park. I’ve been a few times now, and every trip has been different depending on the season.

Must-See Spots in the Finger Lakes

  • Watkins Glen State Park: This place blew me away the first time I visited. The Gorge Trail winds past nineteen waterfalls – some you can even walk behind. I went early in the morning before the crowds and it felt like stepping into a fantasy world. If you do one hike in the Finger Lakes, make it this one. It’s truly one of the most beautiful state parks in New York.
  • Seneca Lake Wine Trail: I spent a whole afternoon hopping from winery to winery here, and it was such a vibe. My favorites were Fox Run for the views, and Glenora Wine Cellars for the atmosphere. If you’re more into beer or cider, there are tons of those options too.
  • Taughannock Falls State Park: I’ll never forget seeing Taughannock Falls for the first time – it’s taller than Niagara! The Gorge Trail is an easy, flat walk and leads you right to the base. If you’re visiting in winter, the falls sometimes freeze, which is magical.
  • Corning Museum of Glass: I didn’t expect to love this as much as I did. Watching live glassblowing was surprisingly mesmerizing, and the exhibits are both artistic and hands-on. If you need a rainy-day activity, this is perfect.
  • Ithaca: This college town has such a fun energy. Between Cornell’s Botanic Gardens, the waterfalls like Buttermilk Falls, and the farm-to-table restaurants downtown, I could easily spend a couple of days here.

Other Spots I Recommend

  • Cayuga Lake Wine Trail: Smaller and less crowded than Seneca Lake, but just as beautiful. I loved sipping wine at Sheldrake Point Winery with views straight out over the lake.
  • Skaneateles: This town felt like a movie set. The water is some of the clearest I’ve ever seen, and the downtown is full of boutique shops and great cafés. Perfect for a leisurely afternoon.
  • Keuka Lake: The Y-shaped lake is unique, and the Keuka Lake Wine Trail has some incredible views. I grabbed a local Riesling here that I still think about.
  • Finger Lakes National Forest: I went hiking here one summer afternoon and barely saw another soul. Rolling hills, wildflowers, and peace and quiet — it was such a refreshing break from the busier parks.

The Finger Lakes are all about local flavors. I had some of the best farm-to-table meals here, especially around Ithaca and Geneva. For wine, Riesling is the star of the region, but I also tried some unique reds and ciders. If you’re a foodie, definitely plan to make dinner reservations at a few of the top wineries or restaurants…they book out quickly in peak season.

Watkins Glen State Park features a dramatic gorge and 19 waterfalls along the Gorge Trail.
Watkins Glen State Park features a dramatic gorge and 19 waterfalls along the Gorge Trail.

Days 18-19: Buffalo and Niagara Falls

By the time I reached Buffalo on my road trip, I honestly didn’t expect much, but this city completely surprised me. With its revitalized waterfront, incredible architecture, and legendary food scene (and nightlife), it ended up being one of the most fun stops of my entire New York loop. And of course, just 30 minutes away, you’ve got Niagara Falls…a natural wonder that truly lives up to the hype.

My Favorite Things to Do in Buffalo

  • Canalside: I loved strolling along the waterfront here. On summer evenings, there were kayaks on the river, live music playing, and food trucks lined up. In winter, it turns into an ice rink, which looked magical.
  • Frank Lloyd Wright’s Darwin D. Martin House: As an architecture fan, this was a must. The tour was fascinating, and it gave me a new appreciation for Wright’s design style.
  • Albright-Knox Art Gallery: I spent a rainy afternoon here, and it was perfect — the collection of modern and contemporary art is world-class.
  • Elmwood Village: I wandered through this neighborhood, stopping at indie shops and grabbing coffee at a local café. It had such a friendly, creative vibe.
  • Buffalo Wings: Of course, I had to try the city’s most famous food. I went to Anchor Bar (where they were invented) and Duff’s, and both were excellent — crispy, spicy, messy, and perfect with a cold beer.

Niagara Falls Highlights

  • Niagara Falls State Park: The moment I walked up to the viewing area and saw the sheer power of the falls, I was in awe. Photos don’t do it justice. The Maid of the Mist boat ride got me absolutely soaked — but it was worth every second.
  • Cave of the Winds: This was one of my favorite experiences. Walking right up to the Bridal Veil Falls on wooden platforms, with water thundering down around me, was unreal. I left drenched but grinning from ear to ear.
  • Niagara Gorge Trail: I hiked a section of this trail, and it gave me an entirely different perspective of the river below the falls. If you love nature, this is a must.
  • Old Fort Niagara: A fascinating piece of history perched where the Niagara River meets Lake Ontario. I learned a lot about colonial-era battles and got some incredible views across the lake.
  • Whirlpool State Park: I stopped here for a picnic and couldn’t believe the swirling rapids below. It’s quieter than the main falls area and a nice break from the crowds.

I absolutely love Niagara Falls, and recommend it to all my friends as a must-do in NY!

    Niagara Falls State Park features observation points, the Maid of the Mist boat ride, and the Cave of the Winds tour.
    Niagara Falls State Park features observation points, the Maid of the Mist boat ride, and the Cave of the Winds tour.

    Days 20-21: Chautauqua-Allegheny Region

    For the last stretch of my New York State road trip, I headed south to the Chautauqua–Allegheny Region…and it felt like the perfect finale. This corner of the state has a slower pace, with wide-open forests, quiet lakes, and a surprising amount of culture. After the buzz of Buffalo and the roar of Niagara Falls, I loved winding down here with a couple of days of outdoor adventures and small-town charm.

    My Favorite Stops in Chautauqua–Allegheny

    • Chautauqua Institution: I visited in the summer when the grounds were alive with lectures, concerts, and people relaxing on porches. Walking through this historic lakeside community felt like stepping back in time — but in the best way.
    • Chautauqua Lake: One of the prettiest lakes I’ve seen in upstate New York. I spent an afternoon kayaking near Bemus Point and then grabbed dinner at a lakeside restaurant as the sun went down. It was the most relaxing evening of the whole trip.
    • National Comedy Center (Jamestown): I wasn’t sure what to expect, but this ended up being one of the most fun museums I’ve ever been to. Interactive exhibits let me try my hand at joke-writing, and there were amazing displays on everyone from Lucille Ball to modern comedians.
    • Lucille Ball Desi Arnaz Museum: As an “I Love Lucy” fan, this was a must. Seeing original costumes and sets was such a nostalgic highlight.
    • Allegheny State Park: Hiking here reminded me of the Adirondacks but with way fewer people. I went in the fall, and the foliage was absolutely stunning.

    Other Places I Loved Exploring

    • Panama Rocks Scenic Park: A quirky natural park filled with towering rocks and narrow passageways. I felt like a kid scrambling around here.
    • Lake Erie Wine Country: I drove the wine trail along the lake and stopped at a few small wineries. It was quiet, scenic, and a nice change of pace from the Finger Lakes.
    • Griffis Sculpture Park: Over 250 massive sculptures spread out across meadows and forests. Wandering through here was both eerie and beautiful.

    I rented a cozy cabin near Chautauqua Lake, which was perfect for ending the road trip. Waking up to the sound of birds on the water was a peaceful reset before heading back toward NYC. If you prefer hotels, the Athenaeum Hotel at the Chautauqua Institution is a beautiful historic option.

      Chautauqua Lake offers boating, fishing, and kayaking, with stunning fall foliage and dining options in Bemus Point.
      Chautauqua Lake offers boating, fishing, and kayaking, with stunning fall foliage and dining options in Bemus Point.

      The Ride Back to New York City

      As my New York State road trip wound down, I realized the drive back to NYC could be just as fun as the destinations themselves. Depending on how much time you have left, you can make this a quick return or stretch it out with a few final stops. I’ve done it both ways…once powering through in a single day, and another time meandering back with scenic detours that made the end of the trip feel like a bonus adventure.

      Route 1: Scenic Southern Route (I-86 and I-81)

      I took this route once in the fall, and the rolling hills of the Southern Tier were glowing with red and gold leaves. A couple of favorite stops along the way:

      • Corning Museum of Glass: Even if you’ve already been, this place is worth a repeat visit. Watching glassblowers at work is mesmerizing.
      • Watkins Glen State Park: Stretching my legs here before a long drive was the best decision. Walking the gorge trail one more time felt like the perfect goodbye to New York’s natural beauty.
      • Binghamton: A quirky stop with old carousels and the Bundy Museum of History and Art, which is full of surprises.

      Route 2: Northern Route (I-90 and I-87)

      On another trip, I looped back through Albany and the Hudson Valley. It’s a bit more urban, but there’s plenty to see along the way:

      • Albany: If you missed it earlier, touring the State Capitol is well worth the stop.
      • Hudson Valley: I swung by the Storm King Art Center for one last walk before heading back to the city — an amazing way to balance out the long drive.
      • Woodstock: I grabbed lunch here at a cozy café, browsed some galleries, and stretched the road trip vibe a little longer.

      My Pro Tip: If you are short on time, leaving early in the morning helps you beat traffic as you get closer to NYC.

      If You Have Time: Spend 2-3 Nights in Long Island

      On one of my New York State road trips, I extended the adventure with a couple of nights on Long Island…and I’m so glad I did. After weeks of mountains, waterfalls, and lakes, it was the perfect way to slow down and enjoy some coastal charm before heading back to the bustle of NYC. Long Island really surprised me with how much variety it offers: beaches, wineries, charming villages, and even a totally different pace of life than upstate.

      Here are some of my favorite Long Island destinations:

      The Hamptons

      I spent a night in East Hampton, and it felt like a completely different world. The beaches in the Hamptons are pristine, with soft sand and endless ocean views. I stopped by Montauk to see the iconic lighthouse, and Sag Harbor stole my heart with its little shops and seafood restaurants. It’s upscale, sure, but you can still enjoy it on a budget if you plan right…I grabbed lunch from a casual seafood shack and it was just as memorable as any fine-dining spot.

      North Fork Wine Country

      If you love wine like I do, this is a must. I spent a day touring vineyards along the North Fork, sipping rosé at Wölffer Estate and sampling reds at Bedell Cellars. The countryside is gorgeous, and Greenport is such a fun town to wander through with its maritime vibe and artsy little shops. It reminded me a lot of the Finger Lakes but with a coastal twist.

      Fire Island

      One of my favorite side trips was taking the ferry to Fire Island. There are no cars, which immediately makes it feel more relaxed. I rented a bike, pedaled along the boardwalks, and spent the afternoon at the beach. It was exactly the kind of peaceful break I needed at the end of a long road trip.

      Other Stops I Loved

      • Huntington: I checked out the Heckscher Museum of Art and wandered through Caumsett State Historic Park Preserve — a beautiful place for a short hike with ocean views.
      • Jones Beach State Park: A classic Long Island experience. Walking along the 2-mile boardwalk at sunset was the perfect way to cap off my stay.

      For accommodations, consider staying at Gurney’s Montauk Resort & Seawater Spa for a luxurious beachfront experience or opt for a cozy bed-and-breakfast in Greenport for a more intimate stay.

      Visit the iconic Montauk Lighthouse to experience its historic charm and stunning coastal views.
      Visit the iconic Montauk Lighthouse to experience its historic charm and stunning coastal views.

      Things to Consider When Planning Your New York State Road Trip

      After driving all over New York State, from the Hudson Valley vineyards to the roaring power of Niagara Falls, I’ve picked up a few lessons that make a huge difference when planning this road trip. Here are the key things I always keep in mind:

      Where to Start Your Road Trip

      I’ve started this road trip in a few different places, but the best launch point really depends on your time and interests:

      • New York City: The most obvious choice. It’s easy to rent a car here, and you can roll right into the Hudson Valley and Catskills within a couple of hours.
      • Buffalo: If you want to kick things off with Niagara Falls, Buffalo makes sense as your starting point. That’s how I structured one of my trips.
      • Albany: Great if you’re more into history and want a smaller, less hectic city to start in.
      • Rochester: This worked perfectly for me once when I wanted to dive straight into the Finger Lakes.

      Best Time of Year for a New York State Road Trip

      I’ve road-tripped New York in every season, and each one brings something different:

      • Spring (April–June): The waterfalls are at their strongest, wildflowers are blooming, and the crowds are light. I love spring trips because everything feels fresh.
      • Summer (July–August): Lakes, wineries, and state parks are at their liveliest. I camped a lot during summer, but it does get busy and more expensive, especially around Lake George and the Finger Lakes.
      • Fall (September–October): My personal favorite. The foliage in the Adirondacks and Catskills is next-level, and the crisp air makes hiking so much more enjoyable.
      • Winter (November–March): If you’re into skiing or snowboarding, Whiteface Mountain and the Catskills are amazing. I’ve also loved cozying up in cabins during snowy road trips. Just be ready for icy roads.

      Number of Days for a New York State Road Trip

      How much time you have really shapes the trip:

      • 1 Week: I’d focus on NYC, the Hudson Valley, and maybe one big natural highlight like Niagara Falls or the Finger Lakes.
      • 2 Weeks: This feels like the sweet spot if you want variety without rushing — Hudson Valley, Catskills, Adirondacks, and a couple of days in the Finger Lakes or Niagara.
      • 3 Weeks: My favorite way to do it. You can see everything — NYC, Hudson Valley, Catskills, Adirondacks, Thousand Islands, Finger Lakes, and Niagara Falls — plus still have time for detours and hidden gems.
      Montauk, at Long Island's eastern tip, offers beautiful beaches, hiking trails, and fresh seafood.
      Montauk, at Long Island’s eastern tip, offers beautiful beaches, hiking trails, and fresh seafood.

      FAQs About Planning a New York State Road Trip

      Planning a road trip through New York State is super exciting, but you might have some questions. Here are answers to common questions to help you plan your adventure.

      What kind of car is best for a New York State road trip?

      I’ve done this road trip in both a small sedan and an SUV. A compact car works fine for cities and highways, but if you’re planning on hitting the Adirondacks, Catskills, or winter roads, I’d go with a small SUV with good traction. It made me feel a lot more comfortable on mountain roads, especially in late fall when the weather can change quickly.

      How many days do you really need for a New York State road trip?

      I’ve done this trip in as little as a week and as long as three weeks. If you only have 7 days, focus on NYC, the Hudson Valley, and one major natural area like the Adirondacks or Finger Lakes. With 2 weeks, you can balance cities, mountains, and wine country without feeling rushed. For the full experience, I recommend 3 weeks…that gave me time to explore every corner, from Niagara Falls to the Thousand Islands, and still take detours.

      Is it worth visiting both the Adirondacks and the Catskills on the same trip?

      Yes, but only if you have the time. I’ve done both in one trip, and while they’re both mountain regions, the vibe is very different. The Catskills feel closer to NYC, with artsy small towns and accessible hikes. The Adirondacks are wilder and more rugged…Lake Placid alone is worth the detour. If you have less than 10 days, I’d stick to one or the other to avoid too much driving.

      Saratoga Springs boasts mineral springs and a lively arts scene in a charming setting.
      Saratoga Springs boasts mineral springs and a lively arts scene in a charming setting.

      Are there tolls on New York State roads?

      Yes, especially if you’re driving along the New York State Thruway (I-87/I-90). I always bring an E-ZPass, which makes things much easier and often cheaper. You can pay cash or card, but having the pass saves time. If you’re renting a car, some companies let you add one for a small fee.

      How expensive is a road trip in New York State?

      It can be as budget-friendly or as luxe as you want. I’ve camped in state parks for $20 a night, and I’ve also splurged on lakefront resorts in the Finger Lakes. Gas and tolls add up, but food can be affordable if you mix casual diners and farm-to-table spots with a few special meals. Wineries usually charge $5–15 for tastings, which I found pretty reasonable.

      What’s the biggest mistake people make when planning this trip?

      The first time I did this, I underestimated how big New York State is. Driving from NYC to Niagara Falls in one go took me 7+ hours…not fun. Now, I always build in buffer days and avoid cramming too many regions into one short trip. My advice: slow down and enjoy each region instead of rushing to check everything off.

      Embark on an unforgettable 3-week New York State journey through this road trip itinerary
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      Jon Miksis

      About Jon Miksis

      Award-winning Travel Writer • Founder of Global Viewpoint • 70+ countries visited • 10 Million+ readers

      Since 2017, I’ve traveled 3–6 months a year, sharing detailed guides that have helped over 10 million readers travel smarter, deeper, and better. My work blends firsthand experiences — from U.S. road trips and cold-plunge cabins to Michelin-starred dining and business-class flights — with honest, independent reviews.

      I’ve been hired by leading tourism boards in 7 countries across Europe, North America, and South America, as well as international travel brands. My travel tips and insights have been featured in Forbes, HuffPost, Yahoo Travel, and The Boston Globe. I’ve personally reviewed 500+ hotels, retreats, and flight experiences — and I never recommend a place I wouldn’t return to myself.

      I also save $5–10K per year on airfare using flight tools and 10+ travel credit cards, and I’ve invested over $100K into personal development through transformational retreats and coaching since 2021.

      When I’m not road-tripping across the Northeast or writing guides for Global Viewpoint, you’ll find me cold plunging in local lakes, sipping espresso in quiet cafes in Vienna, or chasing fall foliage across New England. I split my time between exploring the world and soaking up life in Boston, my lifelong home base. Some of my favorite places I keep going back to? Switzerland, Spain, Iceland, Italy, Greece, the Faroe Islands, Guatemala, California, Montana, Vermont, and coastal Maine in autumn.

      See my latest adventures on Instagram and TikTok.

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