Day Trips from Boston

By Cameron Sperance, author of Moon 52 Things to Do in Boston
Sometimes you just need an afternoon away to feel refreshed. If you’re looking for adventures close to home that you can fit into a single day, here are some day trips ideas that are all easy to get to from Boston.

Get transcendental at Walden Pond

Why go: Visiting Walden Pond is a perfect way to experience the great outdoors (and literary history) within minutes of some of the most congested streets of Boston and Cambridge.
Where: The Walden Pond State Reservation is about a half-hour northwest of Boston and Cambridge, accessible via Route 2 from Cambridge and via Interstates 90 and 95 from Boston. The Massachusetts State Parks service offers the most up-to-date information on trails, parking, and hours of operation.
Timing: The park is open year-round for walks, running, and hiking, but summer is the best time to visit if you want to swim or boat in the pond. If you do head up in the summer, be sure to arrive early—parking lots fill up quickly! Boat ramps are closed from early December through early April.

Roughly half an hour from Harvard Square is Walden Pond State Reservation, just outside the town of Concord. Made famous by the transcendentalist Henry David Thoreau who wrote Walden; or, Life in the Woods here in the 1850s, beautiful Walden Pond has become a favorite destination for Bostonians looking to de-stress and unwind while enjoying the simple beauty of nature.

Go beyond Harvard Yard in Cambridge and Somerville

Why go: Harvard and MIT are the two visitor magnets for Cambridge, a city separated from Boston by the Charles River. But these storied learning institutions have fueled a building boom in Cambridge and the neighboring city of Somerville, which have become lovely towns with exciting restaurant scenes and plenty of charm.
Where: The easiest way to get to Cambridge and Somerville is on the MBTA’s Red Line subway. Most Cambridge destinations are within walking distance of three stops (Kendall, Central Square, and Harvard), while Somerville’s best hotspots are found near the Davis MBTA station.
Timing: Autumn strolls around Cambridge and Somerville are the most scenic, with the changing leaves and the spectacle of the Head of the Charles Regatta. But winter is a good time to curl up in a cozy Harvard Square restaurant or Davis Square speakeasy. Spring can be rather hectic, especially during graduation season. Visit in summer to get sunny days without as many students.

Harvard Square and nearby Davis Square in Somerville (two stops north on the MBTA Red Line subway) have always been popular with college students, but they are also becoming more popular with the post-grad crowd. The growing food scene, fun nightlife, and an array of interesting shopping options surrounded by historic buildings all lend to the youthful energy here.

Get inspired at Mass MoCA

Why go: The Massachusetts Museum of Contemporary Art is a great, cultural motivation to head to western Massachusetts for a day or, even better, a weekend to explore the surrounding Berkshires region.
Where: Mass MoCA is a little over two-and-a-half hours northwest of Boston on Route 2. The easiest way to get there is to drive. • 1040 Mass MoCA Way, North Adams, 413/662-2111
Timing: Fall is my favorite time to visit the museum, as it is also a perfect time to take in the colorful foliage in the Berkshires. But there is plenty to do year-round and particularly in non-winter months: Mass MoCA offers live events with dance and musical performances 40 weekends out of the year. You can spend at least an entire afternoon at the museum but incorporating it into a weekend trip is even better.

You may not expect one of the biggest forces of contemporary art in New England to be well beyond the confines of Boston’s urban core, but the Massachusetts Museum of Contemporary Art, also known as Mass MoCA, is just that: 26 restored, red-brick factory buildings in the Berkshires enclave of North Adams, packed with modern art.

Find quintessential New England in Newburyport

aerial view of historic downtown area of newburyport massachussetts
Historic downtown area of Newburyport, MA. Photo © Jiawangkun/Dreamstime.

Why go: For the varied group torn between a beach getaway or finding a cute town in which to shop and dine, Newburyport has a little bit of everything for everyone.
Where: Newburyport is a 45-minute drive north of Boston near the New Hampshire border on the Atlantic Ocean coast. It can also be reached in just over an hour on the commuter rail from Boston’s North Station.
Timing: Newburyport and Plum Island can be enjoyed year-round.

There are oodles of cute seaside towns up and down the coast of New England—yet I find myself returning, at least once a year, to Newburyport and adjoining Plum Island. The mix of boutique shopping, cobblestoned streets, delectable restaurants, and seaside views in just a few blocks packs a lot into this coastal enclave. Nearby Plum Island is a barrier island and home to some of the more popular beaches where Newburyport locals go in the warmer months. The sandy dunes and expansive coastline make this a great spot for beach picnicking, sunbathing, and playing in the waves.

Go apple-picking

Why go: A fall apple-picking trek is a treasured New England pastime.
Where: Carver Hill Orchard, 101 Brookside Ave., Stow, 978/897-6177 • Smolak Farms, 315 S Bradford St., North Andover, 978/682-6332 • Dowse Farms 30 Rockwood St., Sherborn, 508/653-2639
Timing: September and October are the best times to visit the orchards, but some, like Carver Hill Orchard, begin their picking season as early as July.

Apple-picking season is one of my favorite times to get just beyond the city and collect ingredients for some impressive farm-to-table pies. Lucky for me (and for you), there are several farms less than an hour outside Boston to satisfy fruit and cider cravings. No matter the farm, you’ll need to purchase their empty bags and containers, varying in size (typically $10-30), before venturing out into the orchards and farms for fresh produce. Fruit and veggie ripeness and availability are dependent on weather from year to year, so each year can bring an unexpected surprise, like late-season fruit, or an unpleasant disappointment, like fewer fruity options than you hoped. It’s never a bad idea to call ahead to see what’s in season and ready for picking!

Slurp oysters in Wellfleet

Why go: Nantucket, Martha’s Vineyard, and areas “down Cape” tend to get the heaviest summer crowds, as visitors flock to their beaches. Even Provincetown, at the very end of Cape Cod, gets packed due to its relatively easy access via the Provincetown Fast Ferry. But Wellfleet is known for more than just beaches. Its eponymous oyster is a mainstay in seafood restaurants, so head straight to the source to slurp down a dozen (or more) of these briny delicacies.
Where: Bostonians reliably use the flexed arm as a Cape Cod map, and Wellfleet is about halfway up the forearm. It’s about a two-hour drive from downtown Boston.
Timing: Wellfleet is a fairly easy day trip, especially if you’re planning on timing your visit around OysterFest in October. Leave Boston by mid-morning to arrive just in time for lunch. The late afternoon drive home can be longer, especially in peak summer months when traffic on Route 6 backs up from everyone leaving the Cape.

The Wellfleet Oyster is an integral part of any New England restaurant menu, as these smooth bivalves are a popular meal starter. Often overlooked by crowds passing through en route to Provincetown to the north, the fishing town of Wellfleet is the mecca of the authentic New England oyster experience. From beach shacks to fine dining, the Wellfleet Oyster’s namesake town offers many ways to enjoy a few of these salty gems of the sea.

Cruise Cape Cod on Old King’s Highway

cars on route 6a headed to cape cod in fall
Route 6A in Sandwich, MA. Photo © Smitty411/Dreamstime.

Why go: The path that became Cape Cod’s Route 6A, or the Old King’s Highway, predates the founding of America and gives drivers a sense of what life on the Cape looked like before the rush of tourists, surf shops, and lobster shacks along the Cape’s more bustling roadways.
Where: Route 6A runs 34 miles from the Sagamore Bridge in Bourne to the Orleans rotary. It banks north for the final 28 miles to Provincetown.
Timing: If you don’t mind traffic, the peak summer travel season is the best time to visit due to the seasonality of some of the shops and restaurants along the way. But locals prefer the spring and fall shoulder seasons to avoid crowds.

While those clamoring to get to Provincetown on the Outer Cape as fast as possible might hop on the modern Route 6 to avoid stoplights, Route 6A (also known as the Old King’s Highway) provides a leisurely way to get a sense of the old Cape before it became a summer vacation hotspot. The highway starts in Bourne and meanders east through historic districts of quaint Cape Cod towns. It eventually banks north, and finally ends in Provincetown. The winding drive along scenic beaches, cranberry bogs, and town centers is a great alternative to the modernized highway of nearby Route 6.

Head East on the Mohawk Trail

Why go: Opened in late 1914, the Mohawk Trail is New England’s first official scenic route. The 63-mile stretch passes through 50,000 acres of Massachusetts state parks and forests, offering a variety of seasonal attractions for year-round enjoyment.
Where: Start the Mohawk Trail near Taconic Trail State Park on the Massachusetts/New York border, a roughly three-hour drive northwest of Boston via Interstate 90 and Route 7.
Timing: Take advantage of the chance to admire the natural beauty of fall foliage on your drive by cruising the Mohawk Trail in September and October.

Few things are better than loading the car up with tasty snacks, listening to a great playlist or audiobook, and cruising down the highway, enjoying beautiful views. In Massachusetts, a simple road trip is made even better when combined with cute towns, stunning landscapes, and famous historical landmarks. The Mohawk Trail, less romantically known as Route 2, offers the perfect 63-mile stretch through Massachusetts state parks and forests to make your scenic drive dreams come true.

Take in fall foliage

Why go: Driving to see fall foliage, or “leaf peeping,” brings millions of visitors each year to admire the vibrant changing colors of trees across much of New England. Why not see it for yourself?
Where: Fall foliage can be observed anywhere in New England, from the trees of Boston Common to open fields in northern Vermont. But scenic drives in New Hampshire or Maine are some of the best and most popular options for taking in fall foliage.
Timing: Leaves typically begin to change into their autumn coats of yellow, orange, and red in northern New England in September, while in areas farther south, the leaves turn a little later in the season. Most leaves have usually dropped by November, depending on when the first major frost or snow occurs.

Once you start to see the first hint of red or orange on a tree in New England, brace yourself: leaf peeping season has begun—and it’s serious business. The pumpkin spice lattes flow through the streets, plaid dancing troupes frolic through town, and apple cider donuts are the only thing you’ll find on local menus. Okay, I’m exaggerating—but not by much!

Plaid does tend to get a little more prevalent in the local sartorial spirit during these crisp months, and you will notice a significant spike in pumpkin-flavored anything on menus. This is also when many locals head to area farms for apple- and pumpkin-picking. And throngs of people take to the roads and head out of the city to Vermont, New Hampshire, and Maine to catch the first fall foliage of the season. If you want to join in (and you should; the foliage here can’t be beat), you have several options for a lovely scenic drive.

Shop local in Portsmouth, NH

sunset over the waterfront in portsmouth new hampsire
Portsmouth waterfront. Photo © Alpegor/Dreamstime.
Why go: Skip the outlet malls and support local shops in a charming waterfront town.
Where: Portsmouth is roughly an hour’s drive north of Boston on Interstate 95. It’s the northernmost city on the New Hampshire coast before you cross the border into Maine.
Timing: Warmer months are typically the best for strolling through downtown Portsmouth, but there is something idyllic about holiday shopping in the cold of December.

It’s easy to pass up Portsmouth, New Hampshire, as a weekend getaway opportunity when compared to the bigger Portland, Maine, to the north or Providence, Rhode Island, to the south. But this charming seaside city offers a jam-packed day trip’s worth of shopping opportunities. It’s also fun to just stroll along the streets and admire the many window displays in the lovely boutiques.

Portsmouth is only an hour-long drive from Boston—on paper. I can’t stress enough that timing is everything here, as leaving basically anytime between 3pm and 6pm can turn this into a multi-hour voyage. Make a day of it and leave before breakfast to avoid traffic. Getting out of the city in the morning isn’t typically an issue, as most commuters are heading into the city.

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