The Ultimate New England Road Trip Itinerary in 2021

by Global Viewpoint
New England road trip itinerary

From coastal cities and towns to mountain resorts, New England is the perfect place for road trips. Once the cold weather is behind us, Bostonians like myself set out for day trips, weekend getaways, and even multi-week road trips to see all this region has to offer. That’s why I’ve created this ultimate New England road trip itinerary, which covers all six states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont.

Though you’ll need at least 3-4 weeks to see it all, you can cover a lot of ground in just a few days. Most people don’t have time to finish it all in one go, so I recommend breaking it up into a few separate trips this summer and fall.

For more in-depth guides on day trips and weekend getaways from Boston, check out these two articles below.

Now, without further ado, let’s take a road trip around ‘wicked awesome’ region of New England!

The ultimate New England Road Trip Itinerary pinterest image

Disclosure: Due to COVID-19, there may be travel restrictions in certain areas. Before booking any travels, be sure to follow relevant government guidance and safety protocols.

New England road trip itinerary map

The map below shows all the main stops along this New England road trip itinerary.

Days 1-2: Boston, Massachusetts

Start your New England road trip itinerary in the beautiful city of Boston. It’s home to Logan International Airport and a variety of rental car companies, so most visitors will inevitably begin their adventure here.

The Boston Public Garden is a must-see in the heart of Boston.
The Boston Public Garden is a must-see in the heart of Boston.

As the largest city in New England, Boston is a hub of culture, history, architecture, and food. It’s a bustling world-class city with a small town feel to it. Here are my favorite spots in Boston that you should check out:

The Freedom Trail: 2.5-mile walking path around historic sites and museums. Be sure to eat at either Union Oyster House or Warren Tavern, which are among the coolest restaurants in Boston!

Beacon Hill: A historic neighborhood with iconic brick buildings. There are some amazing Airbnbs and VRBOs in this part of Boston MA!

Boston Common and Public Garden: Scenic public parks in the heart of Boston.

Faneuil Hall: A historic marketplace filled with restaurants and street food vendors.

Boston Harborwalk: A waterfront promenade with stunning views of the Boston skyline.

Charles River Esplanade: Another popular path for a stroll or bike ride. If you have time, head over to Cambridge that lies on the other side of the Charles River.

Newbury Street: An upscale shopping street lined with boutiques and restaurants.

Rose Kennedy Greenway: A public space lined with greenery, food trucks, and more.

The North End: Boston’s version of “Little Italy” with amazing Italian restaurants.

From its colonial heritage to its hip cultural scene, Boston has plenty of cool things to see and do that will keep you entertained for at least a couple of days. Then, you will be ready to explore more of New England.

Read next: 11 Unique Stays in Massachusetts

Acorn Street in Boston is one of the most photographed streets in the US.
Acorn Street in Boston is one of the most photographed streets in the US.
Check out my Etsy shop for a high-resolution wall print or canvas: https://www.etsy.com/listing/793958266/acorn-street-in-boston-massachusetts

Day 3: Salem, Rockport, and Gloucester, Massachusetts

Salem, Massachusetts is a top New England road trip destination

Home to the notorious Salem Witch Trials that occurred in the late 1600s, Salem is a must-see for history enthusiasts. This coastal city brims with historic landmarks, museums, shops, and restaurants that can be covered in a few hours. Here are some sights most visitors will not want to miss:

Salem Maritime National Historic Site: A cluster of 12 historic structures along the Salem Harbor waterfront.

Salem Witch Museum: A museum set inside a 17th-century home that covers the Salem Witch Trials.

The House of the Seven Gables: A colonial mansion built in 1668 that was made famous by Nathaniel Hawthorne’s novel, The House of the Seven Gables.

Peabody Essex Museum: One of New England’s largest museums, home to a vast collection of American and Asian art.

With all its witch-themed museums and shops, Salem has a bewitching feel to it (especially in October around Halloween). But even if witch paraphernalia isn’t your thing, you’ll still appreciate the authentic New England charm of one of America’s oldest fishing villages.

The House of the Seven Gables in Salem, Massachusetts.
The House of the Seven Gables in Salem, Massachusetts.

Gloucester, Massachusetts

Just northeast of Salem is Gloucester, a popular beach destination amongst locals. Two noteworthy beaches to visit on a hot summer’s day are Good Harbor and Wingaersheek. Most beachgoers prefer Good Harbor, but Wingaersheek is preferable for families with small children because there’s very little of an undertow.

Apart from relaxing on the beach, the main things to do in Gloucester are eating seafood and checking out the iconic Fisherman’s Memorial Monument. Then, head next door to Rockport.

The Gloucester Fisherman's Memorial and monument.
The Gloucester Fisherman’s Memorial pays tribute to all the local fisherman who lost their lives at sea. Hundreds of names are inscribed around the memorial; it’s really moving and shocking to see.

Rockport, Massachusetts

Rockport is the quintessential New England town. It is set on the windswept Atlantic coastline and is chock-full of quaint shops, galleries, and restaurants. Drawing visitors with its seaside village vibe and lingering smell of fresh seafood, Rockport is one of my favorite day trips over the summer.

Here’s what you should check out in Rockport, Massachusetts:

Bearskin Neck: The main shopping street in Rockport lined with shops and eateries.

Motif Number 1: An iconic red fishing shack that perfectly complements the surrounding landscape.

Halibut Point State Park: A conservation area with scenic walking trails.

Front Beach: A small beach within walking distance of Rockport’s downtown.

Long Beach: A longer beach (haha) that connects Rockport and Gloucester.

Rockport can get pretty crowded over the summer, so it pays to get there early when the shops open.

Listen to the waves and seagulls, eat a lobster roll, and soak in the charm of one of America’s finest fishing villages.

Motif Number 1 is nestled along Bradley Wharf in Rockport.
Motif Number 1 is nestled along Bradley Wharf in Rockport.

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Day 4: Coastal Byway, New Hampshire

Nestled between Maine and Massachusetts, New Hampshire’s Coastal Byway extends just 18.5 miles along the Atlantic shoreline. Here, you’ll pass by several beaches, historic forts and mansions, and state parks.

These are some of the top things you should see along New Hampshire’s Coastal Byway:

Hampton Beach: A beach resort town with a bustling beach and boardwalk.

Odiorne Point State Park: A beautiful state park along New Hampshire’s rocky coast.

Strawbery Banke Museum: An open-air museum with more than 37 buildings built between the 17th and 19th centuries.

Prescott Park: 10 acres of fields and gardens where summertime concerts are held.

The highlight of any road trip along the Coastal Byway is Portsmouth, a historic city with lots of New England charm. I recommend spending a few hours strolling its cute streets, dining at one of its restaurants, and sampling a local beer or two before continuing north to Maine.

Tugboats in Portsmouth, New Hampshire.
Tugboats in Portsmouth, New Hampshire.

Day 5: York, Ogunquit, and Kennebunkport, Maine

A New England road trip itinerary wouldn’t be complete without visiting Maine. It’s nicknamed “the way life should be,” and you’ll quickly find out why as you venture up its striking coastline.

Perkins Cove in Ogunquit, Maine.
Perkins Cove in Ogunquit, Maine.

Spend at least a day exploring Maine’s southern coast, stopping by seaside towns like York, Ogunquit, and Kennebunkport. These are some of my absolute favorite beach towns in ME. Here are some of the coolest spots in this region:

The Marginal Way: A scenic, coastal trail in Ogunquit. It’s a must-see place on a Maine road trip itinerary.

Perkins Cove: A tiny cove with fishing boats, classic boutiques, and restaurants that serve some of New England’s freshest seafood. Clam chowder and lobster, anyone?

Nubble Lighthouse: An iconic New England lighthouse in York, Maine.

Ogunquit Beach: A vast stretch of beach perfect for swimming (that is, if you’re brave enough to take a dip in the freezing cold water. Welcome to Maine!).

You can easily cover these places as a day trip or weekend getaway from Boston. They are also convenient stops along the way to Portland and Bar Harbor, Maine, which lie ahead on this New England road trip itinerary.

The Marginal Way in Ogunquit, Maine.
The Marginal Way in Ogunquit, Maine.

Day 6: Portland, Maine

Located 45 minutes north of Ogunquit and 2 hours from Boston, Portland is an awesome place to spend a day or weekend.

This seaport city is home to an eclectic mix of museums, art galleries, breweries, and restaurants. Portland is best known for its Old Port—the historic center of town— dotted with quaint cobblestone streets and brick buildings from a bygone era. Here, you’ll also find plenty of eateries serving traditional, Maine-style seafood. Yum!

If you’re into craft beer, you should also check out Portland’s brewery scene, which includes well-known brewing companies like Allagash, Bissel Brothers, and Shipyard.

Portland is also a great destination for sightseeing, where you can hop aboard a ferry to explore Casco Bay, or even drive down the road to check out Portland Head Lighthouse.

From Portland, it’s just a 3-hour drive to Bar Harbor and Acadia National Park, which is the highlight of any New England road trip itinerary.

Tip: On the way up to Acadia from Portland, be sure to make a stop in Freeport, Maine. This town is home to the L.L. Bean Flagship Store, and lots of other outlet stores.

Portland Head Lighthouse is a must-see on this New England road trip itinerary.
Portland Head Lighthouse

Days 7-9: Bar Harbor & Acadia National Park, Maine

Acadia National Park is New England at its finest. This treasure in northeastern Maine is home to some of America’s most incredible biodiversity and landscapes. You should plan to spend at least 2-3 nights here to cover the main sights. Though if you want to take your time and see all that Acadia and Bar Harbor have to offer, I’d recommend spending up to a week here.

Jordan Pond in Acadia National Park is a highlight of any New England road trip itinerary.
Jordan Pond in Acadia National Park.

In the same day, you can witness the power of the ocean as waves batter rugged cliffs and then venture inland to see your reflection in the park’s crystal clear lakes and streams. Here are some must-see sights in Acadia National Park:

Park Loop Road: The main scenic road that crisscrosses the park.

Cadillac Mountain: A mountain with sweeping views of the Atlantic shoreline. For part of the year, it’s the first place in the U.S. where you can see the sunrise. It’s an awesome place to catch the sunrise and sunset (though be warned: in the summer, the sun rises at 4:30am).

Cadillac Mountain is a must-see on a New England road trip itinerary.
Cadillac Mountain is a must-see on a New England road trip itinerary.

Jordan Pond: A pristine lake with crystal clear water and a backdrop of mountains in the background. On a clear day, the visibility underwater can be between 45-60 feet.

Thunder Hole: A rocky inlet that lets out a thunderous roar when waves crash against it. (Note: your best chance of hearing this “thunder” sound is about two hours before high tide).

Sand Beach: A small beach tucked between mountains and rocky shoreline.

Eagle Lake: A gorgeous lake along Acadia’s scenic Carriage Road.

During your trip to Acadia, you will likely stay in Bar Harbor, a coastal town near the park entrance. Lined with cozy shops, restaurants, and B&Bs, Bar Harbor has a wonderful summertime ambiance.

On the way back to New Hampshire, consider stopping at Baxter State Park, which lies further inland. It’s home to Maine’s highest mountain, Mount Katahdin (5,267 feet – 1,605 m) and a variety of fun hikes. The next section outlines this destination further.

Eagle Lake is one of my favorite spots in Acadia National Park.
Eagle Lake is one of my favorite spots in Acadia National Park.

Alternative Road Trip Suggestion in Northern Maine: Baxter State Park

Looking to venture inland from the coastal highlights of ME? Add onto your New England road trip by making a stop at Baxter State Park. This vast wilderness area is home to Maine’s tallest mountain, Mt. Katahdin, and a host of other landscapes including forests, lakes, ponds, rivers, and streams.

Beautiful waterfront views with Katahdin as a backdrop.

Baxter State Park is the northernmost point of the Appalachian Trail. It’s an awesome destination for hiking, camping, fishing, and more. Stay in a log cabin overlooking a glacial lake or a campsite with views of the crown jewel, Katahdin. Though this state park is often overlooked for the coastal cities, towns, and nature areas in ME, it shouldn’t be missed if you have the time!

With over 200,000 acres of pristine woodland, it’s easy to see why Baxter State Park deserves a mention among the best New England road trips.

Days 10-12: White Mountains, New Hampshire

The White Mountains region is a year-round destination on the east coast. It’s especially picturesque during the fall foliage season, but it’s also the perfect getaway in the summer for hiking and camping (and of course, in the winter for skiing). Here are some unique places to explore:

Kancamagus Highway: Take a fall foliage tour on this 35-mile scenic route where you’ll pass by beautiful forests, creeks, gorges, and waterfalls. It’s one of my favorite places to see the fall foliage in New England, when the fields and mountains are covered in red, orange, and yellow leaves.

Omni Mount Washington Resort: A historic and luxurious hotel that’s considered one of the most iconic buildings in New England.

North Conway: A town hailed for its retail outlets and antique shops. There are lots of amazing NH cabin rentals in this region that will give you a proper taste of the White Mountains!

The White Mountains are a popular place for leaf peeping in the fall.
The White Mountains are a popular place for leaf peeping in the fall.

Clark’s Trading Post: A family-run trading post that’s basically a mini-theme park.

Franconia Notch State Park: A stunning park with miles of hiking, biking, and skiing trails. It’s a great stop during a fall road trip itinerary. This state park is home to Cannon Mountain, a 4,000 ft. (1,240 m) peak with a tramway that brings you to the top.

Another place worth noting is the Mount Washington Observatory, which lies on New Hampshire’s highest mountain, Mount Washington (6,288 feet – 1,916 m). It’s infamous for having the most extreme weather conditions on Earth. The highest wind gust ever recorded in the world (231 mph) occurred there in 1934.

There is so much to see in New Hampshire, that you can easily spend a week or more doing a road trip around the whole state.

Built in 1902, the Mount Washington Resort is a must-see in Bretton Woods, New Hampshire.
Built in 1902, the Mount Washington Resort is a must-see in Bretton Woods, New Hampshire.

Alternative Northeast Road Trip Suggestion in NH: The Lakes Region

Unlike the White Mountains, which is known for its adventure and dramatic mountain landscapes, the Lakes Region is a bit more subdued. Sure you’ll find plenty of scenic mountains and outdoor activities, but the main draw is its lakes. If you’re looking to relax and unwind lakeside rather than pedal to the metal, this is the perfect place to visit.

Lake Winnipesaukee has some epic vacation rentals!
Lake Winnipesaukee has some epic vacation rentals!

Spend a weekend or longer at one of the 270 bodies of water that are scattered throughout the Lakes Region. The most famous among them is Lake Winnipesaukee, the largest lake in New Hampshire. Other popular lakes include Lake Sunapee, Ossipee Lake, Squam Lake, and Newfound Lake. Each of these lakes are year-round destinations with plenty of places to eat, shop, explore, and soak up the sun.

If you’re looking to go-go-go on this New England road trip, perhaps choose the White Mountains instead this time around. As this is one of those destinations where you’ll want to salivate over slowly.

Take a step back to relax and savor the moment from an Airbnb or VRBO rental on Lake Winnipesaukee. It won’t be long until you see why this is one of the top places to visit on a New England tour!

The Lakes Region is a top New England road trip idea for those seeking a respite from busy modern life
The Lakes Region is a top New England road trip for those seeking a respite from busy modern life.

Days 13-15: Stowe and Burlington, Vermont

After exploring the White Mountains, head west to Vermont. You’ll be amazed by what you see!

Stowe, Vermont is a top destination on a New England road trip itinerary

Stowe is a year-round destination that makes you feel like you’re in Austria. It’s home to the Trapp Family Lodge, a mountain resort with amazing alpine views and Austrian-inspired food. Vermont is known for its farm-to-table dining, and you’ll find some of the best of it here and in Burlington. Here’s what you should check out:

Mount Mansfield: The highest mountain in Vermont that offers hiking, zip lining, and mountain climbing. Be sure to take the Stowe Mountain Auto Toll Road up to the top.

Alchemist Brewery: A small, family-run brewery that’s best known for its flagship double IPA, the Heady Topper. At 8% ABV, it certainly packs a punch, so make sure you have a designated driver!

Stowe Recreation Path: A lovely 5-mile path made for bike riding and hiking.

Smuggler’s Notch State Park: A popular sightseeing area in the mountains with verdant forests and raging waterfalls. When I was younger, I loved staying at the Smugglers’ Notch Resort.

After spending at least one night in Stowe, head west to Burlington. Admire the gently rolling hills and mountains, and don’t forget to stop by the Ben and Jerry’s Factory in Waterbury!

The Innsbruck Inn definitely makes you feel like you're in Austria.
The Innsbruck Inn definitely makes you feel like you’re in Austria.

Burlington, Vermont

Located on the shores of Lake Champlain, Burlington is an earthy-crunchy city with lots to offer on a New England and Vermont road trip. Burlington is very forward-thinking, as it was the first U.S. city to run entirely on renewable energy. It’s also a popular place for shopping, boating, eating, and drinking. Here’s what you should see and do:

Church Street Marketplace: The main pedestrian shopping street in Burlington that’s jam-packed with shops and restaurants.

Burlington Farmers Market: A local market held every Saturday where delicious produce, meats, and treats are sold.

Burlington Bike Path: A bike path with stunning views of Lake Champlain.

Pub crawl/brewery tours: Consider sampling the city’s renowned craft beer at places like Foam Brewers, Zero Gravity, and Switchback Brewing Company.

Lake Champlain: A large and pretty lake where you can partake in watersports, fishing, and boat cruises. Stay at a cabin overlooking this lake in VT, and you’ll never want to leave!

Burlington, Vermont is a must on a New England road trip itinerary.
Burlington straddles the shores of Lake Champlain.

Be sure to give yourself plenty of time to indulge in Burlington’s culinary scene. It’s truly a foodie’s paradise, where you’re guaranteed to find delicious food wherever you go. And it’s basically all organic and locally-sourced, too. If you’re a dessert lover, Lake Champlain Chocolates is a must! And don’t even get me started on Vermont’s apple picking scene!

Also, if you have time (and a passport), head across the border to nearby Montreal and Quebec City.

Church Street in Burlington, Vermont.
Church Street in Burlington, Vermont.

Day 16: Manchester, Vermont

The next big bucket list item on this New England road trip itinerary is the Berkshires in Western, Massachusetts. It’s about 3.5 hours south of Burlington, so I recommend breaking up the journey by spending a night in Manchester, Vermont.

This quaint town is nestled in the heart of the Green Mountains. It’s known for its cozy inns and precious scenery. Consider checking out Stratton Mountain, Equinox Mountain, and Lye Brook Falls Trail, but don’t forget to relax and soak in the pastoral views, too.

If you’re willing to deviate a bit from this strictly New England road trip itinerary, consider stopping by Lake George and Saratoga Springs, New York, which are just over an hour away.

The Green Mountains is a sought-after destination for seeing the fall foliage.
The Green Mountains is a sought-after destination for seeing the fall foliage.

Days 17-19: The Berkshires, Massachusetts – a must-see on a New England Road Trip Itinerary

The Berkshires is another must-see destination in New England. Situated in Western, Massachusetts, this region spans from the border of Vermont to that of Connecticut. It hosts a variety of amazing outdoor activities, museums, and eateries. Here are some things you’ll want to see and experience in the Berkshires:

Downtown Stockbridge and Great Barrington: A pair of charming, New England towns in the heart of the Berkshires.

Mass MoCa Museum: A factory-turned-museum in North Adams that holds one of the largest contemporary art galleries in the U.S.

Hancock Shaker Village: A historic village built in the 1700s that sheds light on the rustic lifestyles of the Shakers (a Christian sect that is somewhat similar to the Quakers).

Norman Rockwell Museum: A museum dedicated to Norman Rockwell, an acclaimed American painter.

Whitewater rafting on the Deerfield River: A fun summer activity for adventure-seekers.

Mount Greylock State Reservation: Home to the tallest mountain in Massachusetts, Mt. Greylock (3,489 ft. – 1069 m). On a clear day, you can see five states from the top: Massachusetts, Vermont, New York, New Hampshire, and Connecticut.

Canoe or Kayak Tour: A peaceful way to experience the Housatonic River.

The Berkshires brims with spectacular nature.
Nature flourishes in the Berkshires.

Whether you’re into outdoor adventures, farm-to-table dining, or cool cultural sites, the Berkshires is a nice place to visit on a New England or Massachusetts road trip.

For more information on the Berkshires (especially during the fall foliage season), read my article: Fall in the Berkshires.

Hancock Shaker Village in the Berkshires.
Hancock Shaker Village in the Berkshires.

Days 20-21: Connecticut Coast Scenic Drive, Connecticut

Though often overlooked by many New England visitors, Connecticut has no shortage of coastal cities and towns that make for the perfect summer road trip. For the full CT experience, stay in a cabin overlooking farmland and rolling hills or a cottage on the ocean.

Sheffield Island Lighthouse in Norwalk lies along the Connecticut Coast Scenic Drive.
Sheffield Island Lighthouse in Norwalk, Connecticut.

Begin this scenic coastal drive in Greenwich, which lies near the New York state border, and head east towards Mystic and Stonington. It’s about a three-hour, 120-mile journey from one end to the other, but it’s well worth it for the sweeping ocean views. Here are some places you may want to stop along the way (ordered from west to east):

Greenwich: A coastal town steeped in rich history and culture. It’s one of the wealthiest communities in the country.

Fairfield: A college town with beautiful beaches, homes, and scenery.

Silver Sands State Park: Three miles of boardwalk through marshland, beaches, and sand dunes.

Branford: A town known for its expansive beaches and breweries. It’s also an excellent location for catching the sunrise.

Guilford: A historic town jam-packed with shops, restaurants, and parks.

Hammonasset Beach State Park: A 2-mile stretch of beaches in Madison, Connecticut.

Westbrook: A quaint community with sandy beaches and cozy B&Bs along the waterfront.

East Lyme: Home to Rocky Neck State Park, which contains more than 700 acres of marshland, beaches, and rocky shorelines.

Mystic Seaport: A historic village with a unique maritime legacy. If you’re into gambling, consider spending a night at nearby Foxwoods or Mohegan Sun casinos.

Stonington: A beautiful seaside village and a good place to end your adventure along the Connecticut Coast Scenic Drive.

Once you make it to the end of this coastal drive, you’ll be within reach of the Rhode Island border.

Connecticut Coast Scenic Drive is often glossed over on most New England road trip itineraries.
Connecticut Coast Scenic Drive is often glossed over on New England road trip itineraries, but it shouldn’t be.

Day 22: Block Island, Rhode Island

Located off the coast of Rhode Island, Block Island is one of New England’s best hidden gems. It has the classic New England vibes of Martha’s Vineyard and Nantucket, without the crowds.

This island is steeped in pristine scenery and Victorian charm, hosting a variety of cool sights including windswept beaches, historic lighthouses, and rustic farms.

Block Island is an off-the-beaten-path destination on this New England road trip itinerary.
The National Hotel is the flagship Victorian-era hotel on Block Island.

Interestingly, there are no stoplights or international chains on Block Island. It hasn’t changed all that much since the late-1800s, except for a few cars and electricity.

Many New Englanders visit Block Island as a day trip, but you can spend the night as well. To get there, take a ferry from any of the following places:

Point Judith, Rhode Island (www.blockislandferry.com)

Newport, Rhode Island (www.blockislandferry.com)

New London, Connecticut (www.goblockisland.com)   

Fall River, Massachusetts (www.blockislandferry.com)

At this stage of your New England road trip, you’re probably ready for some R&R. There’s no better place to recharge your batteries than a secluded island getaway like Block Island.

The Mohegan Bluffs are clay cliffs that are about 150 feet high.
The Mohegan Bluffs are clay cliffs that are about 150 feet high.

Days 23-24: Newport, Rhode Island

On your New England road trip itinerary, I recommend spending at least a day or two in Newport, Rhode Island. It’s best known for its Gilded Age mansions built during the late 19th century. Here’s what you need to see:

The Breakers: The most iconic home in Newport. It was built as a summer residence for the Vanderbilt family, one of America’s wealthiest and most powerful families.

The Breakers is about as lavish as a mansion can get.
The Breakers in Newport is about as lavish as a mansion can get.

Marble House: Another must-see mansion built from 500,000 cubic feet of marble.

Cliff Walk: A 3.5-mile walkway that connects many mansions with Newport’s scenic waterfront.

Rosecliff: An ornate mansion that was filmed in the 1974 film, The Great Gatsby.

Ocean Drive Historic District: A 10-mile scenic drive along the coastline.

Though Newport is a great place to spend a couple of nights, it’s also close enough to Boston for a day trip.

Newport is a must-see on this New England road trip itinerary.
Rosecliff Mansion in Newport, Rhode Island.

Days 25-28 Cape Cod, Massachusetts

I love the Cape. Since I was a kid, I’ve always enjoyed spending weekends there over the summer.

Take the Old King’s Highway (Route 6A), and you’ll pass by miles of scenic coastline paired with historic seaside villages. Continue on Rt. 6 all the way to Provincetown, which lies at the tip of the Cape. Here’s where you should visit along the way:

Cape Cod Canal: A 7-mile canal that connects Cape Cod with the Massachusetts mainland. There’s a nice bike path that runs on both sides of the canal.

Sandwich Village: The oldest town on the Cape dating back to the 1600s. Here, you’ll find many historic homes and B&Bs. There are also popular museums like the Sandwich Glass Museums and Heritage Museums & Gardens.

Falmouth: A beach resort town in the Upper Cape with miles of beautiful shoreline.

Hyannis: A popular tourist destination that’s often called the “capital of the Cape.”

Dennis: Another beach resort town worth checking out.

Cape Cod Rail Trail: A bike trail that runs through Dennis, Harwich, Brewster, and Orleans.

Chatham: This cute town is where I got married. It’s definitely one of my favorite places on the Cape!

Nickerson State Park: A campsite with pretty ponds and hiking trails.

Orleans: A beach town that faces the Atlantic Ocean and Cape Cod Bay, where you’ll be able to experience the warm and cold water on both sides of the Cape.

Provincetown: A lively town known for its art and music scene. Here, you’ll also find unique sights like Race Point Lighthouse, Race Point Beach, and the Pilgrim Monument. There are many incredible lighthouses to choose from in this part of the Cape. Also, don’t miss Dune Shacks Trail, which is among the top hikes in New England!

A beach in Provincetown, also known as P-Town. It's an awesome place for a New England road trip itinerary.
A beach in Provincetown, also known as P-Town.

Whale Watching: There are many whale watching cruises that leave from Hyannis, Barnstable, and Provincetown. I did the Dolphin Fleet Whale Watch from Provincetown. It’s a must when you’re visiting the Cape.

Also, you can take a ferry to the nearby islands of Martha’s Vineyard or Nantucket. Both islands are hot getaways for the rich and famous. On Martha’s Vineyard, be sure to do your sightseeing aboard a moped!

Read next: 17 best vacation rentals in Cape Cod

Martha's Vineyard is known for these colorful gingerbread cottages. It's a must-visit on this New England road trip itinerary.
Martha’s Vineyard is known for these colorful gingerbread cottages.

Last stop on this New England road trip itinerary: Plymouth, Massachusetts

Let’s wrap up this New England road trip by bringing it back to where it all began.

Plymouth, Massachusetts was the site of the first Pilgrim settlement in 1620 (the town is celebrating its 400th birthday this year). There’s a rock left behind that marks the spot where the first settlers arrived, which is a bit underwhelming, but nevertheless worth seeing if you’re a history buff. Apparently, some of my ancestors arrived there on the Mayflower. Fun fact!

Plymouth Rock is a great place to wrap up this New England road trip itinerary before heading back to Boston.
Plymouth Rock

At a high-level, here’s a map showing this New England road trip itinerary.

New England road trip map
New England road trip map.

Other destinations to consider if you have time

If you’ve got more time and want to see more that New England has to offer, consider visiting these other cool places below:

Providence, RI: The capital of Rhode Island, home to Brown University, historic architecture, and a cool art and nightlife scene.

Lake Winnipesaukee, NH: The largest lake in New Hampshire, located in the heart of the Lakes Region.

Woodstock, VT: A quaint town in central Vermont with historic buildings and beautiful scenery.

Lubec, ME: The easternmost town in the United States.

New England road trip itineraries in 2021

Hope you enjoyed my guide on the Ultimate New England Road Trip Itinerary! This should keep you busy for quite a while, and when you’ve tackled it all, feel free to check out these other New England articles for more inspiration:

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2 comments

Daniela June 22, 2020 - 16:55

You live in such a beautiful part of the country! Always enjoy reading your travel guides.

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Global Viewpoint June 25, 2020 - 08:39

Thank you, Daniela! 🙂

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