15 Best Day Trips from Boston, Massachusetts

by Global Viewpoint
Best day trips from Boston

Why you should do day trips from Boston

Nestled in the heart of New England, Boston is a great launchpad for day trips to explore the best of the region. It’s one of the few places where you can see skyscrapers, hit the beach, hike mountains, and explore historic settlements all in one day. As a native Bostonian, people often ask me about the best day trips from Boston. The truth is, there’s so much to see near the city that it’s hard to narrow down just a few day trip ideas. So instead of just choosing a handful, here’s a round-up of the 15 best day trips from Boston. I listed them in order of their proximity to the city.

Note: The public transportation in Boston will not take you to many of these places. As such, I recommend renting a car, doing a guided tour, or meeting a friendly local who will show you around!

Looking for somewhere cool to stay in/around Boston? Check out these amazing Airbnbs in Massachusetts!

The Berkshires in Western, Massachusetts is one of the best road trips from Boston.
The Berkshires in Western, Massachusetts is one of the best road trips from Boston.

1. Cambridge, Massachusetts (5 minutes)

Just across the Charles River from Boston is an equally unique and historically significant city called Cambridge.

Cambridge is best known for its world-class universities, namely Harvard and MIT. You can easily spend half the day exploring these prestigious campuses, each offering beautiful architecture, spacious parks, and interesting museums. Afterwards, make your way to places like Harvard Square and Central Square, where you can grab a drink or bite to eat. If you wish, take something to go and find a nice spot on the Charles River, preferably with a view of the Boston skyline. It’s especially beautiful during the fall foliage months once the leaves change color.

In Cambridge, there’s truly no shortage of cool cultural and historical sights, which can even rival those across the river in Boston. I recommend spending at least a day here, if not longer, which is why I decided to include Cambridge on this list of the best day trips from Boston.

2. Lexington and Concord (30-45 minutes)

If you’re from the US, this pair of towns probably rings a bell. The American Revolutionary War began in Lexington and Concord in 1775, paving the way to America’s independence from Great Britain. Both towns are steeped in history, deserving a spot in this list among the best Boston day trips.

Lexington, Massachusetts: A Day Trip from Boston Steeped in Rich History

Known as the “birthplace of American liberty,” Lexington is where the first shots of the war were fired. It’s home to more than 10 battle sites and memorials where you can learn about the Minute Men and their skirmishes against the British Red Coats.

Some must-see sights in Lexington include Lexington Green, the grounds of the first battle, Buckman Tavern, a historic-tavern-turned-museum, and Hancock-Clarke House, a colonial building where John Hancock and Sam Adams once stayed.

Today, this upscale town is walkable and bike-friendly, and you can enjoy classic New England scenery in between historic sites. Be sure to also stop by Wilson Farm, a local market known for its fresh produce and delicious baked goods.

Lexington Minuteman Statue in the Battle Green
The Lexington Minuteman Statue stands in the Lexington Battle Green. Though erected to symbolize the generic Minuteman, it’s now said to represent John Parker, the militia officer who commanded the colonial troops at the Battle of Lexington in 1775.

Concord, Massachusetts

Home to the Minute Man National Historical Park, Concord is another popular place to learn about America’s roots. However, aside from the really old stuff, this town is also cherished for its more recent past. During the 19th century, many notable figures in literature and philosophy lived here, including Ralph Waldo Emerson and Henry David Thoreau. Today, you can visit their homes and check out famous sights like Walden Pond and the Sleepy Hollow Cemetery.

Whether you’re a history buff or someone who just enjoys the outdoors, Concord is a great place to spend part of your day trip from Boston.

Concord is a wonderful short day trip idea from Boston.
The Old North Bridge in Concord is a replica of the one which stood here during the Battle of Concord. It crosses the Concord River inside the Minute Man National Historic Park.

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3. Salem, Massachusetts (45 minutes)

Even if you’ve never visited Massachusetts, you’ve probably heard of Salem. This coastal city is infamous for the witch trials that occurred in the 1600s. To this day, you’ll find no shortage of witch-themed museums, shops, and tours here, making it one of the best day trips in New England.

During Halloween, Salem is teeming with haunted hayrides, witch trial reenactments, and candlelit ghost tours. If you don’t have a chance to visit then, you can still get your fix at places like the Salem Witch Museum and Witch Dungeon Museum. You also can’t miss The House of the Seven Gables, a 17th-century mansion made famous by Nathaniel Hawthorne’s novel.

Salem is one of the best day trips from Boston.
Built in 1668, the House of the Seven Gables is one of the top attractions in Salem, Massachusetts.

If you’re not into the witch trial era, there’s plenty of other unique attractions to explore in Salem. From the Customs House and warehouses to the endless docks and fishing boats, the city’s maritime heritage is on full display. Salem was once a bigger port than Boston, where merchants would bring fine arts from as far away as China. A vast collection of Asian, African, and Oceanic art is stored inside the Peabody Essex Museum, which also merits a visit while visiting here.

Whether you’re into fishing villages, old architecture, or superstitious stuff, consider taking a walking tour of Salem, one of the best short day trips from Boston.

The Friendship of Salem is an iconic ship in Salem, Massachusetts.
Built in 2000, the Friendship of Salem is a replica of the 1797 East Indiaman vessel. It’s docked at the Salem Maritime National Historic Site.

4. Rockport, Massachusetts (1 hour)

Known for its coastal charm and historic downtown area, Rockport is the perfect day trip from Boston.

As its name suggests, Rockport is a rocky enclave surrounded on three sides by the Atlantic. It’s the quintessential New England town, where you’ll find some of the best clam chowder and lobster around.

However, what sets Rockport apart from other coastal communities is that it’s also an art colony. As such, you’ll find lots of art galleries, shops, and museums scattered around this quaint town. For the shopaholics out there, look no further than Main Street, where you’ll find an endless supply of giftshops selling everything from clothing and jewelry to fudge and ice cream.

Whether you’re there for the beach, seafood, art, or all the above, Rockport is a great place to spend a few hours before continuing onto these other popular day trips near Boston.

Rockport is one of the best road trips from Boston.
Rockport, Massachusetts is among the best day trips from Boston.

5. Gloucester, Massachusetts (1 hour)

Unlike Rockport, which is on the quaint and touristy side, Gloucester has an almost gritty feel to it. With 400 years of maritime history, it’s the oldest fishing port in America. The place perpetually smells like fish, and that’s part of what makes it so enticing for locals and visitors.

If you’re visiting Gloucester during the summer, you’ll quickly take note of all the beach traffic. Good Harbor and Wingaersheek are two popular beaches, the latter being more for families with young children (due to its small waves). Good Harbor, my favorite beach in the Northshore, has an island where you can walk to during low tide. Gloucester is also known for its whale watching, where you’re all but guaranteed to see them.

On a rainy New England day, you may want to check out the city’s museums, such as the Beauport (the Sleeper-McCann House) and Cape Ann Museum. Gloucester is even home to a medieval castle, the Hammond Castle, which looks more like it belongs in Europe than the US. (Read my article about the most beautiful castles in the world here).

If you’re seeking a dose of beach and history on a summer holiday, look no further than Gloucester as one of the best day trips in Massachusetts.

The Fisherman’s Memorial is an 8-foot tall bronze fisherman, and an iconic symbol of Gloucester. It was erected to commemorate more than 10,000 Gloucester fisherman who have died at sea, including those featured in the Hollywood blockbuster, The Perfect Storm.

5. Newburyport, Massachusetts (1 hour): One of the Best Boston Day Trips

Newburyport is another seaside town north of the city. It’s among the best short day trips from Boston. However, unlike Rockport and Gloucester which draw the crowds, Newburyport is a hidden gem on this list of the best day trips from Boston.

Originally a shipping port, Newburyport has a well-preserved historic center with buildings dating back hundreds of years. Old churches stand alongside spacious parks, while upscale shops and restaurants are popping up by the dozens. Though a gentrified town today, it still retains much of its coastal New England charm from centuries past.

Less than 2 miles from downtown Newburyport is Plum Island, one of the top attractions nearby. Plum Island is known for its beach plum shrubs (hence the island’s name) and sand dunes, which can reach as high as 50 feet (15 m). It’s also known to be one of the best places for birdwatching in the region.

Aside from its sweeping coastal views, Newburyport is also popular for its shopping and dining. As such, it’s a great place to visit during all times of the year, rain or shine.

There are lots of other things to do in the area, but these are some of my favorite things about taking a day trip from Boston to Newburyport.

6. Nashoba Valley Vineyards (1 hour)

Massachusetts isn’t the first place that comes to mind when you think of wine country. However, Nashoba Valley—just an hour outside of Boston—is home to a fantastic family-run vineyard that’s perfect for day-trippers.

At the Nashoba Valley Winery, you can taste some of the region’s top wines, all while soaking in the scenic countryside setting. You can also pick apples, peaches, and nectarines when they’re in season.

Unlike other local vineyards, Nashoba Valley Winery is open year-round. In the winter, you can go skiing and tubing during the day, and enjoy wine and farm-to-table dining at night. What more could you want in a winter day trip from Boston?

(Check out my article of the best wine regions in the world)

Nashoba Valley Winery is one of the best day trips and road trips from Boston.
If you’re into wine paired with stunning scenery, consider a day trip to Nashoba Valley Winery.

7. Wrentham Outlets (1 hour)

If you’re a shopaholic or looking to check off your holiday shopping list, consider a trip to the Wrentham Outlets. Home to more than 170 stores, this open-air shopping center is the largest in New England.

Here, you’ll find everything from everyday clothing brands to high-end luxury retailers. Popular stores include Vineyard Vines, Michael Kors, American Eagle Outfitters, and the Nike Factory.

The Wrentham Outlets are the perfect short day trip from Boston. Also, given that it’s on the way to Newport, Rhode Island, another destination on this list, you can visit both in one fell swoop. If you’re looking to find a bargain when you’re shopping, these outlets are a great bet.

If you only have time for a short road trip from Boston, consider checking out the Wrentham Outlets.
If you only have time for a short road trip from Boston, consider checking out the Wrentham Outlets.

8. Portsmouth, New Hampshire (1 hour, 10 minutes)

Portsmouth is a coastal city in southern New Hampshire, just over an hour from Boston. As one of New England’s earliest settlements, it was made prosperous by its thriving trade and shipping industry. Today, it’s easily among the best day trips to New Hampshire from Boston.

Portsmouth is compact, yet full of history and seaside charm. As a result, Portsmouth is a very walkable town, perfect for a stroll (except during blizzards and torrential downpour – welcome to New England).

The Portsmouth Harbor Trail, one of the top things to see and do in town, guides you past dozens of historic sites and colonial-era buildings. Some top sights include Market Square, a 17th-century square lined with art galleries, restaurants, and antique shops, and the Strawbery Banke Museum, a collection of historic homes. Once you finish the trail, which isn’t that long, you’ll have many nice restaurants and shops to choose from.

Today, visitors are allured to Portsmouth by its historic, fishing village vibe and authentic, family-owned shops and restaurants. As such, Portsmouth is definitely among the best day trips in New England.

Portsmouth, New Hampshire is one of the top day trips from Boston.
Portsmouth Harbor is one of the main draws to this seaside city.

9. Newport, Rhode Island (1.5 hours): A Romantic Day Trip from Boston

Situated on the southeastern tip of Rhode Island, Newport is the perfect day trip and weekend getaway from Boston. (Check out the best weekend getaways in New England here). It’s best known for its Gilded Age mansions, many of which dangle over rugged, wave-battered cliffs.

In Newport, you’ll have a chance to see lavish manor homes, Italian palazzi, and French châteaux in the same trip. My favorite mansions are The Breakers, Marble House, and Rosecliff, each offering a splendid taste of how the ultra-rich used to live.

The Breakers is among the most magnificent mansions in Newport, Rhode Island.
The Breakers is among the most magnificent mansions in Newport, Rhode Island.

Aside from these decked-out dwellings, Newport is a great place to wander around and soak in the oceanfront views. The Cliff Walk, a 3.5-mile path linking the mansions with the waterfront, is worthy of a stroll, especially when the weather is warm.

Newport is also home to the International Tennis Hall of Fame, which draws tennis fans from all around the world. It was also the site of the first U.S. Open championship in 1881.

The city is especially festive during the holiday season, when the mansions are adorned with Christmas lights and decorations. There’s truly a reason to visit here during all times of the year.

Built in 1898, Rosecliff is one of my favorite mansions in Newport.
Built in 1898, Rosecliff is a must-see mansion on Bellevue Ave in Newport.

10. The southern coast of Maine (1.5 hrs)

Maine’s southern coast is one of the most popular day trips from Boston. Each summer, tourists from far and wide converge on its immaculate beaches, which are among New England’s finest (beware though, the water can be freezing!). Some towns worthy of exploring include Ogunquit and Kennebunkport.

Ogunquit is your classic New England beach town. It’s best known for its scenic coastal trail called the Marginal Way. Another must-see is Perkins Cove, with views over fishing and lobster boats.

Ogunquit is also an artistic community, home to many art galleries and museums, including the Ogunquit Museum of American Art. This place is brimming with jubilant energy in the summer and becomes a ghost town in the winter. Therefore, I only recommend doing day trips here in the late spring, summer, and early fall.

If you want to avoid the crowds, I recommend visiting Ogunquit in the late-spring.
If you want to avoid the crowds, I recommend visiting Ogunquit in the late-spring.

Kennebunkport is another vacation hotspot in Maine. It’s not far from Ogunquit, so you can kill two birds with one stone during your day trip from Boston.

This affluent town is home to beautiful beaches and iconic lighthouses. It also has many boat tours and dining and shopping options to choose from. Upscale shops and art galleries line its streets, while magnificent mansions (including that of former President George H.W. Bush), gently snug the shoreline.

There’s a ton to see here, but it can be covered at a high level during a day trip from Boston. So eat some lobster roll and enjoy all that southern Maine has to offer! Oh, and be sure to see the Nubble Lighthouse too!

Cape Neddick in southern Maine should definitely be on your road trip from Boston.
Built in 1879, Cape Neddick is one of the country’s most iconic lighthouses. Located near Ogunquit and Kennebunkport, this should definitely be on your road trip itinerary from Boston.

11. Cape Cod, Massachusetts (1.5+ hours)

When it comes to road trips from Boston, there may be no better choice than Cape Cod.

Cape Cod is a hook-shaped peninsula in southeastern Massachusetts. It’s comprised of 15 towns and villages, extending from Woods Hole to Provincetown. The Cape is a popular summer retreat amongst Bostonians, and the perfect day trip for visitors of Boston. Here are a couple of places that deserve a visit:

Martha’s Vineyard

Martha’s Vineyard is an island off the coast of Cape Cod. New Englanders and urbanites are drawn to its untouched nature and beautiful beaches. The island is also brimming with charming gingerbread cottages and iconic lighthouses. There’s so much to see around the island, and many of the top sights are packed into two towns, Edgartown and Oak Bluffs.

The preferred mode of transportation here is the moped, which can easily get you around the whole island. In fact, Martha’s Vineyard is known to be one of the most moped-friendly places in the country. If you’re not into mopeds, you can rent bikes, take the public bus, or rely on taxis to get around.

Martha’s Vineyard is accessible by plane or ferry. The ferry ride from Woods Hole takes 45 minutes, and the flight from Boston is under an hour. While a couple of nights is ideal for exploring Martha’s Vineyard, it can be covered in a day as well.

If you're planning to visit Cape Cod, consider making the ferry ride over to Martha's Vineyard.
If you’re planning to visit Cape Cod, consider making the ferry ride over to Martha’s Vineyard.

Provincetown

Provincetown is situated at the very tip of Cape Cod’s hook. Colloquially referred to as P-Town, it’s a popular destination for artists, musicians, and members of the LGBTQ community.

If you’re planning a visit to Provincetown, be sure to carve out enough time to go swimming in Herring Cove. Also, make sure to spend time wandering around town and checking out the local art galleries.

You can get to Provincetown by driving or taking a ferry from Boston, which takes 90 minutes.

Other unique destinations to consider in Cape Cod include Chatham, Hyannis, and Nantucket.

If you’re interested in seeing Cape Cod’s coastline and beaches, consider checking out the Cape Cod National Seashore, Coast Guard Beach (Eastham), and Race Point Beach (Provincetown). These are my favorite stretches of coastline on the Cape, but there are countless other beaches just waiting to be discovered.

Read next: Unique Places to Stay in Cape Cod

Provincetown is among the best and most popular day trips from Boston.
Provincetown is among the best and most popular day trips from Boston.

12. Portland, Maine (2 hours)

Portland is New England at its finest. Like many places on this list of the best day trips from Boston, Portland has a proud maritime heritage. What sets it apart, however, is its diverse assortment of museums and art galleries, greenspaces, and some of New England’s top microbreweries.

If you only have time to do one thing in Portland, be sure to visit the Old Port. This historic center is characterized by quaint cobbled streets and brick buildings. You’ll find many of the city’s top restaurants, bars, and boutiques here.

Portland's Old Port is frozen in time.
Portland’s Old Port is frozen in time.

Another must-see is the Portland Head Lighthouse. Built in 1791, it’s the oldest lighthouse in Maine and among the most iconic on the eastern seaboard.

Whether you’re into old ports, fresh seafood, or good beer, there’s plenty to do in Portland that merits at least a day trip from Boston.

Portland is the perfect road trip idea from Boston.
Portland is the perfect road trip idea from Boston.

13. The Berkshires, Massachusetts (2.5 hours): One of the Best Nature-Filled Day Trips from Boston

If you’re willing to drive 5 hours roundtrip in a day (aggressive, but doable), consider adding the Berkshires to your list of day trips from Boston.

Known for its stunning scenery, the Berkshires is a must-see for nature lovers. It’s especially breathtaking during the fall months, when the leaves change colors amid a backdrop of scenic mountains, rivers, and lakes. So much so, that leaf peeping should be considered a sport here.

The Housatonic River is an amazing place to catch the fall foliage in the Berkshires.
The Housatonic River is an amazing place to catch the fall foliage in the Berkshires.

With a stellar farm-to-table dining scene, the Berkshires is also popular among foodies. Each of the restaurants I’ve been to are supplied by local farmers, so you’ll find some of the freshest ingredients around.

The Berkshires is also known for having a lot of interesting museums. Art and culture are on full display inside the Norman Rockwell Museum, Hancock Shaker Village, and Mass MOCA. Comprised of more than 40 historic buildings, Old Sturbridge Village also deserves a visit.

Whether you’re into nature, food, or food for thought, the Berkshires is one of the best weekend getaways in New England.

Hancock Shaker Village is one of the highlights of a visit to the Berkshires.
Hancock Shaker Village is one of the highlights of a visit to the Berkshires.

14. White Mountains, New Hampshire (2.5 hours)

Unlike the seasonal destinations on this list, the White Mountains in New Hampshire is great to visit during all times of the year. In the summer, people come here for the hiking trails and camping. In the winter, it’s a popular place for skiing. And in the fall, the mountains come alive with stunning fall colors. Though it’s not close enough to Boston to be considered a short day trip, it’s still worthwhile to explore if you’re willing to be out all day.

There are three main parts of this region that are worthy of a day trip, including the Kancamagus Highway, Bretton Woods, and Franconia Range. Here’s why you should visit each region:

  • Kancamagus Highway: The perfect place for fall foliage and hiking. Along this 35-mile highway, you’ll encounter stunning scenery, including dense forests, creeks, gorges, and waterfalls.
  • Bretton Woods: Home to the Omni Mount Washington Resort, which is a destination in and of itself. The Bretton Woods area is a popular destination for outdoor activities such as golfing, zip lining, and skiing.
  • Franconia Range: A popular mountain range for hiking in the summer. Three peaks are over 5,000 feet (1,500 m) elevation.
The Omni Mount Washington Resort is among the most magnificent hotels in New England.
The Omni Mount Washington Resort is among the most magnificent hotels in New England.

In addition to the sub-regions above, there are a couple of towns you won’t want to miss in the White Mountains. Lincoln, a small town on the western side of the Kancamagus Highway, is home to Clark’s Trading Post and Loon Mountain. North Conway, which straddles the highway’s eastern corner, is home to some of the best shopping outlets in New England.

Whether you’re into outdoor adventures or tax-free shopping, you’ll find something to do for the whole family in the White Mountains, one of the best New England day trips.

15. New York City, New York (4 hours)

This is more of a weekend getaway than a day trip from Boston, but I still think New York City deserves a mention on this list. NYC is seamlessly connected to Boston via bus, train, flight, or car — making it feasible to get to and from in a day.

At the very least, you can cover the city’s top sights and landmarks in a few hours, including Central Park, Times Square, the Empire State Building, and the Statue of Liberty. If you’re willing to wake up early and leave late, you’ll have ample time to explore these highlights, and still enjoy a nice lunch at a rooftop terrace in Manhattan.

New York is a bustling cosmopolitan city that definitely warrants a visit when you’re in the northeast.

New York City is a great day trip or weekend getaway from Boston.
Central Park in New York City.

More ideas for Boston day trips

If you’re looking for even more ideas for day trips near Boston, here are a few more:

Freeport, Maine: This is just a short drive from Portland, and it offers some incredible shopping and outdoor adventures. It’s home to the flagship L.L. Bean store, Wolfe’s Neck Woods State Park, and the Desert of Maine. As such, it’s easily one of the best day trips in New England.

Litchfield Hills, Connecticut: This is the ideal Boston road trip idea for outdoor enthusiasts. Here, you can go hiking, fishing, canoeing and even leaf peeping during the fall months.

Marblehead, Massachusetts: This is among the best day trips in Massachusetts if you’re looking for beautiful historic homes and sweeping ocean views.

Best Boston day trips and short getaways

I hope you enjoyed reading this round-up of the best day trips from Boston! There are so many cool and interesting places to choose from, so I did my best to showcase a variety of different experiences. If you have time, also be sure to visit Vermont, one of my favorite New England states. Check out the articles below for more Boston day trips options:

Have you been to New England before? What are your favorite day trips from Boston?

Happy Travels!

Jon


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