16 Thrilling Day Trips from Boston Actually Worth Your Time

As a travel addict who’s lived in the Boston area for over ten years now, I’m constantly on the lookout for worthwhile day trips from Boston. (Yes, even when I’m not traveling, I’m desperately seeking travel.) Lucky for me, there are so many great options up here.

As compact as New England is, there’s no shortage of great reasons to leaving the city for a day and explore someplace totally new (whether you live here like me or are just visiting). But, where do you start? This post covers 16 of the most fun day trips from Boston that are actually worth your precious time and answers some Boston day tripping questions you probably have. Enjoy!

Day trips from Boston: Map

The map below contains all the day trip destinations mentioned in this post so you can best plan your travels. To save this map, click on the star ⭑ next to the map’s title. To use it, open Google Maps on your phone, click “Saved,” then click “Maps.”

Outdoorsy day trips from Boston

If you’re seeking day trips from Boston in the summer, check out these super fun outdoorsy destinations:

1. White Mountains, New Hampshire | Hiking adventures

If you’re looking to do some hiking near Boston, White Mountain National Forest is about as close to alpine as you can get on the East Coast. This range includes 48 peaks over 4,000 feet including the 6,288-foot Mount Washington—the highest peak in the Northeast.  

Start with one of the peaks in the Presidential Range—Mounts Webster, Jackson, or Pierce—or the Franconia Ridge loop trail. (But maybe stay away from Mount Washington, widely known as one of the deadliest hikes in the entire world, and, no, that’s not an exaggeration.)

2. Boston Harbor Islands | Island playgrounds

Even though they’re just right outside of Boston, the 30+ islands and peninsulas of Boston Harbor Islands National and State Park feel a world away. You can catch the BHI ferry from either Long Wharf (by the aquarium) or Southie and the ferry rides take just about half an hour (each way). You can visit spots like:

• Georges Island (spring, summer, & fall) – Home to Fort Warren, a historic Civil War-era fort that also served as a control center during World War II (There’s actually a lot of WWII history in Boston.)
• Thompson Island (spring, summer, & fall) – Haven of nature trails and great views of the Boston skyline
• Spectacle Island (summer only) – Full of fun outdoor activities like hiking, swimming, beaches, and boating
• Peddocks Island (summer only) – Tons of nature, wildlife, and historic structures like Fort Andrews and a WWII-era chapel

3. The Berkshires | Nature & quintessential New England towns

For an easygoing day trip from Boston, consider heading out to the Berkshires. The Berkshires isn’t one specific place, but rather a collection of cities in nature-y Western Mass. All the towns listed below take between 2 to 2.75 hours to get to. Here are a few things you can do on a day trip to the Berkshires:

• Visit the Berkshires Botanical Gardens or the Norman Rockwell Museum in Stockbridge
• Attend the famous Tanglewood Music Festival in Lenox or spend some time in the Pleasant Valley Wildlife Sanctuary
• Head over to Great Barrington to do the Monument Mountain hike or a different hike to check out Bash Bish Falls (the highest waterfall in MA)
• Visit Pittsfield to check out Herman Melville’s former home or the Hancock Shaker Village for some living history
• Bowl a few strings in Shelburne Falls–one of the oldest bowling alleys in the country
• Head up to Mount Greylock for some hiking – the highest point in MA and part of the Appalachian Trail

7. Springfield, Massachusetts | Unique museums

Springfield, MA is another great destination for history lovers if the history you’re most interested in is sports, guns, and/or international tragedy. Hear me out…

What to see & do on a day trip to Springfield, MA

• Basketball Hall of Fame – Did you know basketball was invented here in Springfield, MA? Ergo, the Naismith Memorial Basketball Hall of Fame and its 40,000+ square feet of basketball history.
• Springfield Armory – National Historic Site at the country’s first armory where you can explore centuries of military weaponry.
• Titanic Museum – Check out the collection of rare Titanic survivor artifacts–“one of the finest anywhere,” apparently.

8. Hartford, Connecticut | Lobster & literary history

I took my first day trip to Hartford in 2018 and I couldn’t believe it had taken me so long. (After all, Connecticut is where the lobster roll was invented; what had I been waiting for?) Hartford is the capital of Connecticut, just a 1.5-hour drive from Boston, and home to some really cool museums. While in Hartford, check out:

• Mark Twain House – Cool museum to Mark Twain in the (huge) house he lived in
• Harriet Beecher Stowe Center – Abolitionist and author Harriet Beecher Stowe actually lived right next door to Mark Twain!
• Wadsworth Atheneum Museum of Art – Tons of European and Egyptian art and cool temporary exhibits
• Get a lobster roll for lunch!

Super ambitious day trips from Boston

If all of these day trips from Boston so far have seemed a little too easy and relaxed, might I interest you in more of a challenge? For when you really want a more ambitious day trip from Boston, head to:

9. New York City day trip from Boston

Before you get all That’s crazy! on me, hear me out. I’ve taken a day trip to New York City from Boston a bunch of times and I’m happy to report it’s totally doable! Yes, it’s going to be a long day; and yes, it’s going to be exhausting… but it’s also going to be SO FUN AND EXCITING! Don’t let the distance between the two cities scare you off; at least consider it first.

How to take a day trip from Boston to NYC

NYC may not be the most popular day trip from Boston, but you can’t say it’s not accessible. You can get between the two cities via car, train, a combination of the two (and I’ve done all three), or bus. Travel time is pretty much the same for all: 4 hours.

Boston to NYC by car: It’s a fairly straightforward drive from Boston to NYC, but I’m going to steer you away from this method because:

• Driving the 4 hours back to Boston late after a (long) day trip to New York City is too dangerous
• There’s so much potential for ungodly traffic backups
• You’ll have to pay a ridiculous amount in tolls
• Driving in and around NYC is a nightmare at best
• And so is parking

Boston to NYC by train: The Amtrak from Boston to NYC takes between 3.5 and 4 hours and you don’t have to worry about a thing as far as transportation goes. Just sit back and scroll Instagram until you get there. The main thing I don’t like about this direct train is that it ends in Penn Station instead of Grand Central. (Booo.)

Boston to NYC by car + train: Because I live here and have my own car, this is how I usually make this trip. It’s a two-hour drive from Boston to New Haven, CT where I park my car and hop on the Metro North—the commuter rail system between Manhattan and the CT suburbs. The train ticket is so cheap and parking at the train station is beyond reasonable. (Driving that last two hours home late at night is brutal though.)

Boston to NYC by bus: The Flixbus has several time slots that all take about the same as the other methods and cost much less. It’s always a gamble traveling by bus in the U.S., but it’s still a worthy option.

What to see and do in NYC on a day trip

Well, there’s more to see and do in NYC than literally any other place in this country, so I’ll leave that up to you. (Check out my NYC bucket list here for all the best stuff!) Really, you can do just about anything you can dream of.

Coastal day trips from Boston

Another thing we have in abundance here are charming coastal towns just a short drive away. Consider one of these great destinations for your day trips from Boston.

10. Newport, Rhode Island | Mansions, wine, & sailboats

Newport, RI is going to be the bougiest of your day trips from Boston but also one of the most beautiful. (JFK lived here.) Here’s what to see and do with a day in Newport:

• Walk the cliff walk – Free 3.5-mile walking trail on the coastal cliffs with awesome views
• Visit the Newport mansions – See what sick amount of wealth looks like at the Breakers (owned by the Vanderbilt family), Rosecliff (built for an heiress), and tons more from the gilded age (modeled after French chateaux).
• Visit one of the many wineries – Newport Vineyards and Greenvale Vineyards are my two faves.
• See the Newport coast from a sailboat – I’ve done midday and sunset sails here and loved them both!
• Check out the charming seaside town or take a walking food tour.

11. Portsmouth, New Hampshire | History & dumb guy stuff

Head one hour’s drive from Boston in the other direction to Portsmouth, NH for another coastal day trip from Boston that’s equally charming, delicious, and historic. Here’s what to do here:

• Stroll through beautiful Prescott Park in the spring/summer
• Walk the Black Heritage Trail – Lots of monuments and Underground Railroad sites here
• See the USS Albacore – Unique research submarine
• Eat at Geno’s Chowder Shop, Kaffee Vonsolln (amazing German bakery), and Annabelle’s Ice Cream
• Visit the Museum of Dumb Guy Stuff – Model trains, battle diorama, a big dog; it’s fantastic, trust me.

12. Portland, Maine | Craft beer, great food, & lighthouses

Head even further north of Boston and you’ll be in Portland in southern Maine–another delicious day trip from Boston. Foodies and craft beer junkies, rejoice! Here are some of the top things to do here on a day trip:

• Stop by a craft brewery – Bissell Brothers, Alagash (my personal fave), Definitive, and tons more. (But do so responsibly if returning to Boston means you’ll be driving.)
• Eat at some of the best spots – Duckfat, Eventide Oyster Co., Central Provisions
• Visit the Portland Head Light – Historic lighthouse + gorgeous setting
• And the Portland Museum of Art – See Monet, Jackson Pollock, and more
• Stroll the Old Port – Cafés, shops, lots of things to do

Great Portland tours

• Old Port Culinary Walking Tour – This is such a foodie town; get the most out of it that you can. Or perhaps this Seafood Lovers Tour?
• Two-Hour Guided History Walking Tour
• Maine Lighthouses Sightseeing Cruise – See all the Portland lighthouses from the water! (Includes drinks!)

Best fall day trips from Boston

I’m sure it’s not news to you that New England in the fall is just *chef’s kiss!* And while you should definitely spend more than a day out in our nature this fall, there are still a couple of beautiful day trips you can take from Boston to see the color and soak up the season.

13. Salem, Massachusetts | Halloween central

Though not exactly known for its fall color, Salem, Massachusetts is without a doubt the best day trip to take from Boston in the month of October. Known for its infamous witch trials of the 1600s, Salem is Halloween Central for the entire month. If you’re of the “Halloween is a month-long holiday” belief, definitely plan a day trip to Salem. While here, do the following:

• Visit the Salem Witch Museum – It’s pretty kitschy but still gives you a pretty good idea of what the “Salem Witch Trials” were all about (Included in the Boston GoCity pass.)
• Check out all the Hocus Pocus filming locations – My personal favorite thing to do here.
• Walk around downtown Salem – Check out all the potion stores, magic shops, palm readers, and other spooky spots.
• Pop by the Bewitched statue of Elizabeth Montgomery
• Visit the famous House of the Seven Gables – Built in 1668; Nathaniel Hawthorne wrote a novel about it. (Included in the Boston GoCity pass)

If you’re not into the whole “witch” thing but still want to visit Salem, you can (and should) visit any time of the year. In that case, also consider:

• Visiting the Peabody Essex Museum, a world-renowned art museum (included in the Boston GoCity pass)
• Exploring the Salem Maritime National Historic Site
• Stop by Notch Brewery for some delicious European-style beers (another personal favorite)

How to get from to Salem from Boston

Taking a day trip from Boston to Salem is super easy and you can actually get here four different ways: by car, train, ferry, or small-group day trip.

Boston to Salem by car: Quick and easy 35-minute drive (Rent a car here if you haven’t done so already.)

Boston to Salem by train: Quick and easy 30-minute train ride on the commuter rail leaving from North Station (Newburyport/Rockport line)

Boston to Salem by ferry: 50-minute high-speed ferry ride departing from Long Wharf. I realize this is about twice as long as the other two methods, but it’s great if you don’t want to deal with public transportation, don’t have a car, and want to see Boston from the water (which I recommend). Consider it a sightseeing cruise too!

Boston to Salem with a small-group tour: This highly-rated guided tour of Salem also includes roundtrip ferry transportation (plus a guided walking tour of many of the best Salem sites and admission to the Salem Witch Museum).

Top day trips from Boston for fall foliage

There’s more to New England in the fall than just witches; there’s also vibrant fall color! (…in the woods where the witches hang out, obviously.)

14. The Berkshires (fall edition)

I won’t talk more about what to do on a day trip to the Berkshires since I’ve already done that, but know this is a fantastic day trip to take from Boston in the fall as much as in the summer.

Even if all you do is drive through, you’ll see gorgeous fall foliage. However, these charming Berkshires towns are even more charming in the fall with all their small-town, Stars Hollow vibes. Here’s where to go and what to see in the Berkshires in the fall:

• Drive: Mohawk Trail along Route 2, a historic scenic route
• See: The Bridge of Flowers in Shelburne Falls, MA
• Drive: Berkshires Scenic Byway (Route 7)
• See: Adorable and historic Williamstown
• Drive: to the top of Mount Greylock (MA’s highest point) for awesome views
• Hike: to the top of Mount Greylock, part of the Appalachian Trail

15. White Mountains, NH (fall edition)

Even if you’re not a hiker, the White Mountains of New Hampshire still make one of the best day trips from Boston in the fall due to the insane fall foliage here. Again, all you really have to do is drive. (If that’s all you want to do, of course.) Here’s where to go and what to do:

• Drive: The Kancamagus Highway – Incredibly scenic winding mountain drive
• Hike to: Artist’s Bluff in Franconia Notch State Park – Gorgeous mountain viewpoint
• Drive to: The top of Mount Washington – It’s a super dangerous hike, yes, but driving to the summit via the Mount Washington Auto Road is a popular local activity. Or you can opt for the Cog Railway—the first ever mountain railway.

Cape Cod (beach) day trips from Boston

If you came here looking for info on Cape Cod day trips from Boston, I’m afraid I have bad news. Cape Cod is not a doable day trip from Boston. If you really want to visit the Cape, you’ll need at least a few days. Here’s why:

• Attempting to get from Boston to Cape Cod in the summer literally means hours and hours of sitting in traffic. There are only a couple of (narrow) ways and bridges onto the Cape and the bottleneck is like nothing you’ve ever seen before.
• The Cape is long and the roads are narrow (like, 2 lanes) so it takes a really long time to get anywhere.
• There’s nothing worth seeing here that you can’t see much easier and faster in the other day trips from Boston mentioned in this post.
• This is a summer-only destination. So it’s either mind-numbing traffic or not worth going at all.

16. Provincetown, MA (the one exception)

Provincetown, MA is located on the tippy-tip of Cape Cod and is the only exception for a worthwhile day trip from Boston—because you can take a direct ferry here! Provincetown is a famous LGBTQ getaway and fun summer hot spot. Here’s how to spend a day in Provincetown (still part of the Cape Cod National Seashore):

• Visit the Pilgrim Monument and Provincetown Museum (Did you know the Pilgrims actually landed in Provincetown first? Oops.)
• Spend a beach day at Race Point Beach (and visit Race Point lighthouse)
• Explore the shops and restaurants on Commercial Street
• Eat at the famous Lobster Pot (Anthony Bourdain ate here.)

What about day trips to Nantucket from Boston? Martha’s Vineyard?

Like the Cape, I would never recommend a day trip from Boston to either Nantucket or Martha’s Vineyard. Here’s why:

• These islands aren’t exactly close – The fast ferry is 1 hour to Nantucket and 1 hour 20 minutes to Martha’s Vineyard and the regular ferry to Nantucket is 2 hours and 15 minutes.
• You have to get to the Cape first – Maybe an hour ferry doesn’t sound bad, but first you have to get to the Cape to catch it. For more on that nightmare, see the previous section.
• Getting around these islands just plain sucks – Taxi supply is super limited and demand is super high. It’s not a fun thing.
• It’s expensive – The high-speed ferry alone is $89.

If you want some beach time while you’re here, take the ferry to Provincetown instead. If you want some charming coastal classic New England cities, visit Portsmouth, Newport, or Portland.

Easy day trips from Boston without a car

If you have no plan to rent a car during your visit, here are the best day trips from Boston you can take via other modes of transportation:

• Boston Harbor Islands – Public ferries available from two Boston locations
• Concord & Lexington – If you book one of the small-group tours that include round trip transportation
• Plymouth – If you book this full-day tour
• New York City – Via direct Amtrak train or bus
• Salem – Commuter rail train (Newburyport/Rockport line), high-speed ferry, or small-group tour
• Provincetown – Direct ferry (either high-speed or regular speed)
• New Bedford & Fall River – Train to these cities from Boston coming in 2024 (allegedly)

More info for your Boston trip

• Hotels: Find great places to stay here on Booking.com (though Expedia and Hotels.com have some great deals too).
• Rental cars: Check out the best Boston rental car deals here so you can actually take some of these fabulous day trips!
• Saving money: Save tons of money on your sightseeing here with the Boston GoCity Pass. (And check out all the best things to do in Boston here!)
• Travel planning: Pick up a New England guidebook for all the necessary traveling planning information.

Like this post? Have more questions about taking day trips from Boston? Ask away in the comments. Have a nice (day) trip!

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