20 Day Trips From Boston

Boston is the capital of Massachusetts in New England, in the North East United States. Boston itself is a modern metropolis, yet one steeped in history. Walking between the city’s attractions is the perfect way to explore. From the Boston Red Socks at Fenway Park to the hive of the Seaport District, there’s much to see in Boston.

Boston’s location is also perfect for escaping the city and exploring further afield. Its location is such that there are many exciting day trips from Boston you can take. Fancy a day of whale watching on the Massachusetts coast? You can be there in 45 minutes. In two hours, you can be at Yale University in Connecticut, and believe it or not, you can be in New York City in just three and a half hours. Massachusetts, Rhode Island, Connecticut, New Hampshire, Maine, and New York are states you can visit as day trips from Boston. Here are 20 of my favourite.

20 Day Trips From Boston

Day Trips in Massachusetts

1- Go Whale Watching in Gloucester, MA

The coastal city of Gloucester is located on Cape Ann, just a 45-minute drive northeast of Boston.

The east coast is one of the best places to whale watch in America and you can see these beautiful creatures just a short drive from the Massachusetts capital.

The Stellwagen Bank National Marine Sanctuary in the Atlantic Ocean is one of the top places to go whale watching for humpback, finback and minke whales.

Experienced marine biologists lead the boat trips, so you gain insight into the species and their habitats.

Try a Boston day trip to Gloucester between May and October for the best chance of whale sightings.

Whale tours are extremely popular, so reserve your spot in advance to make sure you don’t miss out on an experience of a lifetime.

Time from Boston: 45 minutes.

2- Spend the Day in Cape Cod, MA

Cape Cod is a hook-shaped peninsular in the southeast of Massachusetts.

An irresistible combination of white sandy dune-backed beaches and delightful coastal towns has made Cape Cod one of Massachusetts’s top attractions.

Just an hour and a quarter drive outside the state capital, you can be at the beginning of the Cape Cod peninsular.

Head to Mayflower Beach for whiter than white sands and emerald waters, or travel to the tip of the peninsular to Race Point Beach (2 hours 10 minutes drive from Boston), to catch some of the best surf waves in Massachusetts.

Wherever you go on the Cape Cod peninsular, bring a picnic, your swim gear, and money for ice cream as you enjoy a day at one of many spectacular beaches.

Time from Boston: 1 hour 30 minutes. Book the fast ferry from Boston to Provincetown for a comfortable way to get to Cape Cod. It has air conditioning, free WiFi and a bar on board.

3- Visit the Literary Town of Concord, MA

Concord, Massachusetts, is one of the closest day trips from Boston you can do.

You’ll arrive in a town known for its literary connections just less than 20 miles (32 km) northwest of Boston and a 30-minute drive.

Concord was the location of four famous literary figures’ homes, notably Orchard House, which Louisa May Alcott, author of Little Women, lived in between 1858 and 1877.

She drafted the hit novel Little Women in this Concord home, so it’s worth seeing for its historical value but as well as visiting this historic literary home, there are plenty of other things to do in the town.

For example, stroll around Walden Pond for vibrant colours and reflections.

Then, visit the Old North Bridge, a monument of the American Revolution or satisfy more of your literary tastes with a visit to the Concord Public Library.

Time from Boston: 30 minutes. This private excursion to the literary town of Concord is a day trip that will satisfy literary fans as many other writers have ties to the town, including Emerson, Thoreau and Hawthorne.

4- Head to Martha’s Vineyard, MA

A day trip from Boston to the island of Martha’s Vineyard will land you in a place visited by the rich, the famous, and those searching for a peaceful retreat.

The small island is off the southern coast of Cape Cod.

From Boston, it takes 1 hour and 15 minutes to drive to Falmouth, from where you board the ferry for a 45-minute trip to Martha’s Vineyard.

The ferry departs from Woods Hole in Falmouth from 6 am every hour and a quarter until 9.45 pm.

Tickets with Steamship Authority are $19 for an adult round-trip and $10 for a child round-trip.

Once on the island, head to the beach, visit the island’s colourful gingerbread houses and relax at Joseph Sylvia State Beach.

Even though the island is small, there are so many things to do on Martha’s Vineyard that you’ll need to leave Boston early to fit them all in.

Time from Boston: about two hours. Book a day trip to Martha’s Vineyard here.

5- Visit Rockport, MA

Rockport is a sleepy seaside town on Cape Ann, Massachusetts, popular with locals as it’s only an hour northeast of Boston.

Visiting Rockport Harbour has to be high on your list.

Motif, the name given to a tiny red fishing shack, is popular among photographers.

Visiting in spring, when the flowers are blooming, is ideal, as this already beautiful area is amplified tenfold.

Wander around Dock Square and you will find a diverse range of art galleries.

There are 30 art galleries in Rockport just waiting to be explored.

With names like Tuna Wharf and Bearskin Neck, you can’t help but love this day trip destination.

Time from Boston: One hour.

6- Spot Witches in Salem, MA

Salem is an excellent place for a day trip from Boston if you’re interested in the supernatural and macabre.

Famous for the 1692 witch trials and a long list of witch-related dramatisations, such as Arthur Miller’s play The Crucible, Salem is a haunt for all things witchcraft, historical and Halloween.

To get a true understanding of this city, start your trip with a visit to the Salem Witch Museum.

You’ll leave an expert on the 1692 Witch Trials but there are some non-witchy things to do in Salem too.

Visit the beautiful Breakheart Reservation, 652 acres (263 ha) of nature, trees, a lake and even a beach.

Don’t bother with breakfast in Boston, grab some delicious food at The Ugly Mug in Salem instead.

The Ugly Mug serves all-day breakfast and brunch and whatever breakfast food you can think of, they’ve got it.

Salem is 25 miles (40 km) northeast of Boston up the I-93 and I-95.

Time from Boston: 30 minutes by car and an hour by ferry. Taking the ferry is an easy way to get to Salem so save the hassle and pre-book your tickets online here.

7- Discover Plymouth, MA

This Boston day trip is just a 45-minutes drive south of the city.

Plymouth played an important part in America’s history as the landing place of the first pilgrims.

The pilgrims who sailed from England on the Mayflower in 1620 first landed at Plymouth Rock.

Now don’t visit expecting to see a rocky cliff face. Plymouth Rock is literally just a rock!

Well, it’s a rock sitting within Massachusetts’s smallest state park in a sort of pillared shrine.

Now don’t misunderstand me, I’m not mocking, but it does look rather insignificant in solitary confinement.

According to legend, this was the very boulder upon which the Pilgrims first landed, and we shall believe it, despite all its potential shortcomings as a theory.

Pack a picnic and enjoy lunch in Nelson Memorial Park.

Wander around the perfectly manicured Brewster Gardens and visit the Plimoth Patuxet living museum.

Time from Boston: 45 minutes. Most organised day trips stop in Quincy, the birthplace of two former US Presidents, Plymouth Rock, Plimoth Patuxet and the Mayflower II. Book your ticket here and skip the line at the museums.

8- Explore Nantucket, MA

Nicknamed ‘The Little Grey Lady of the Sea’, Nantucket is a fantastic day trip to take from Boston.

This small island off the coast of Cape Cod and near Martha’s Vineyard is the ideal rural coastal escape.

Nantucket’s beaches are enough to draw anyone to the island, while the Whaling Museum offers an insight into the depths of our oceans.

Discover the Sankaty Head Light, another of New England’s picturesque lighthouses.

Before you catch the ferry back to the mainland, enjoy a meal at Topper’s, The Wauwinet Hotel’s restaurant.

Drive an hour and a half to Hyannis and take the ferry to Nantucket from Boston.

The high-speed ferry (one hour) costs $75 for a round-trip while the traditional ferry is a lot cheaper at $19.50 but takes 2 hours 15 minutes.

Time from Boston: from 2 hours 30 minutes (including the ferry ride).

Day Trips to Rhode Island

9- Wander Around Newport, RI

Travel 72 miles (115 km) south of Boston and over the border and you’ll arrive in Newport, Rhode Island.

Not only are you getting to visit a great city, but also an island.

Newport sits on the south end of Aquidneck Island and claims to be the “Sailing Capital of the World”, so the city’s busy harbour is well worth a visit.

Take a sailboat tour of Newport harbour to enjoy the city’s famous waters.

Schooner Adirondack II offers a variety of cruise options, from sunset cruises to cocktail cruises, even a whole-day sailing trip.

Gilded Age houses and mansions dot the city.

The Elms, Marble House and The Breakers are all impressive mansions built in the 19th century.

The charming architecture doesn’t stop with the mansions, as characterful boutiques line the streets of Bellevue Avenue, Broadway Street and Thames Street.

One of the fun activities for outdoorsy travellers in Newport is to take the 3.5-mile (5.6 km) cliff walk.

You’ll be treated to expansive sea views, rugged cliffs, and the opportunity to peer in at all the fancy mansions that billionaires call their homes (well, probably second homes).

Time from Boston: 1 hour 30 minutes. Book your day trip to see the Newport mansions.

10- Head to Providence, RI

Why not visit the state capital of Rhode Island on your next day trip from Boston?

Providence became a city in 1636, making it one of the USA’s oldest cities.

There are many things to do in Providence.

The city is home to Ivy League institute Brown University, which has seen notable alumni walk its grounds. Emma Watson, John F. Kennedy Jr, and the current United States Secretary of the Treasury, Janet Yellen, to name a few.

You can explore the RISD Museum, which houses more than 100,000 works of art.

Concentrating on fine art and decorative art, there are plenty of pieces to study and enjoy at RISD. Then head to Providence Athenæum, a beautiful and historic library.

Providence is well renowned for the WaterFire event.

Created by Barnaby Evans, WaterFire is a fire sculpture installation located along the rivers in downtown Providence.

The installation consists of more than 80 floating bonfires.

Dates for the events are released on WaterFire’s website at the end of April and the event usually runs from May to November.

Driving to Providence from Boston takes over an hour or the Amtrak train from South Station in Boston to Providence Station is only 35 to 50 minutes and costs around $24 (though prices vary considerably depending on which time you select).

Time from Boston: 35 minutes to an hour. Book your day trip to Rhode Island.

Day Trips from Connecticut

11- Reminisce About Student Life at Yale University, CT

Yale University is a famous Ivy League institution in New Haven and one of the world’s most prestigious universities.

Yale dates back to 1701 and is the third-oldest university in the USA.

There are so many things to do once at the esteemed school.

Start your trip by visiting all 14 residential colleges on campus.

The campus buildings and accommodation are beautifully historic, especially by American standards.

Be sure to head to the Beinecke Rare Book and Manuscript Library, a striking modern cuboid filled with literary treasures.

Once inside, you’ll be overawed by shelves of rare books stacked from floor to ceiling.

It would feel only right to eat a student style lunch when on campus.

Head to Charley’s Place for a diverse range of global cuisines, or pick either Sally’s Apizza or Frank Pepe’s for some of the best pizza around.

After lunch, head to Chapel Street to the Yale School of Art, where you can check out the student’s artwork. It’s basically a free art gallery.

Before you leave, visit Handsome Dan, the school’s bulldog granite mascot, outside the Yale Bowl (the university football stadium).

Tap his head before you leave for Boston, as it will bring you good luck.

Time from Boston: The journey from Boston to New Haven is around two hours. Just don’t let anyone from Harvard know you’re going to visit their rival, Yale.

12- Visit Hartford, CT

The capital of Connecticut, Hartford, is just an hour and a half drive from Boston.

Surrounded by so many other great New England capitals and cities, Connecticut is often overlooked even though there are many things to see and do in Hartford.

Visit the Mark Twain House & Museum, located in the Victorian Gothic mansion that Twain and his wife lived in between 1874 and 1891, now a museum dedicated to his work and life.

Well-known author Mark Twain was famous for books such as Adventures of Huckleberry Finn, Life on the Mississippi and The Adventures of Tom Sawyer.

The Connecticut Science Centre has over 165 interactive exhibits to keep you entertained for hours.

At this Hartford venue, you’ll surely learn a lot, from space exploration and rocket ships to biological science and brainwaves.

Day Trips to New Hampshire

13- Ski at Attitash Mountain Resort, NH

Attitash Mountain Resort is a fantastic skiing area in the White Mountain National Forest in New Hampshire.

Wake up early and you can be on the slopes by mid-morning for a whole day of skiing.

Located close to the North Conway Village, Attitash Mountain Resort is a great place to enjoy a day on the snow.

This resort is the perfect place to ski for all abilities as there is a variety of meandering green slopes for beginners and pleasurable blue slopes for intermediate skiers.

The more experienced and adventurous skiers or snowboarders can hit the black diamond slopes.

This ski resort is around 150 miles north of Boston. If you’re visiting in the Fall, you’ll want to go on a day trip to the White Mountains to see the stunning fall foliage.

Time from Boston: 2 hours 40 minutes.

14- Spend the Day at Lake Winnipesaukee, NH

If it’s nature you’re after, then head up to Lake Winnipesaukee for the day.

Lake Winnipesaukee, in New Hampshire, is just over two hours driving from Boston.

The lake is the state’s largest body of water and provides plenty of opportunities for fun and exploring.

Take a scenic cruise around the lake. Two and a half hours of gentle cruising allows you to understand how big the lake is and enjoy the beautiful scenery, particularly in rusty orange autumn. Book a fall foliage day trip here.

Visit Gunstock Mountain (located next to the lake) for an adventure in the air.

Zipline above the trees with Gunstocks Zipline Tour, which covers 1.6 miles and can reach speeds of 70mph.

Then head to the Daytona Fun Park for go-karting, high rides and bumper boats.

Time from Boston: over two hours.

15- Hike in the Summer and Ski in Winter at Bretton Woods, NH

Bretton Woods is a well-renowned area within the town of Carroll in New Hampshire and a day trip from Boston for all seasons.

You may have heard of this area in New Hampshire because of the Bretton Woods Agreement created in 1944.

History buffs will know that the Mount Washington Hotel in Bretton Woods was the meeting place of delegates from 44 countries during WWII.

These countries agreed to establish what we know today as the IMF and the World Bank Group to provide financial assistance after the wide-scale destruction of WWII.

History aside, Bretton Woods is a great day trip destination for all seasons.

In winter, the slopes of the White Mountains is an excellent and inclusive place to ski or snowboard.

There’s even a sweet shop, Chutters Candy Store, at the top of one of the runs, where you can stock up on a few sugary indulgences to keep you going on the slopes.

In summer Bretton Woods transforms into a green adventure playground where you can enjoy golf and tennis in the mountain’s foothills. Mountain bike, hike, ride the gondola and enjoy a canopy tour.

The forest is stunning in fall when the leaves turn orange, yellow, brown and gold. Book a fall foliage tour of the White Mountains here.

Time from Boston: 2 hours 30 minutes.

16- Hike Mt. Washington, NH

Mount Washington is New Hampshire’s tallest mountain and hiking to its summit makes for a fantastic, high-energy day trip.

Standing at 6289 ft (1,917 m) this hike is not for the faint-hearted, and your fitness levels will have to be good.

There are several different trails to reach the summit but one of the most popular is the Tuckerman Ravine Trail.

This 6.6-mile trail will undoubtedly take you the whole day, so you will need to be leaving Boston extremely early to squeeze this one in.

The Tuckerman Ravine Trail starts at the Pinkham Notch camp, where you can park your car.

Though gruelling, once you reach the summit, you’ll be convinced that it was worth the sweat and next-day muscle pain, as the views are incredible.

Make sure you plan accordingly, as although this may be on the Boston day trip list, you will have to leave incredibly early to give yourself enough time to hike.

I couldn’t resist putting this spectacular hike on this list of day trips from Boston. You’ll know why when you see the views.

Time from Boston: 3 hours 40 minutes.

Day Trips to Maine

17- Relax on Ogunquit Beach, ME

Drive 1 hour and 20 minutes north of Boston via the I-95 N and you will reach the sleepy town of Ogunquit and a perfect white sandy beach.

In the native Algonquin Indian language, Ogunquit means “beautiful place by the sea”, and this day trip sure is breathtaking.

This sand bar beach, backed by the Ogunquit River Estuary, offers the perfect excuse to escape the city and immerse yourself in coastal nature.

Time from Boston: 1 hour and 20 minutes.

18- Visit the Coastal City of Portland, ME

Spending the day in Portland, Maine, will provide you with a taste of what the state has to offer.

It just takes 1 hour and 45 minutes to reach Portland from Boston.

You’ll feel instantly relaxed when you’ve arrived, as this coastal city has a stress-free atmosphere.

I suppose its ambience is something to do with being by the sea, there’s just something about that sea breeze that oozes calm and happiness.

A chalky coloured lighthouse sitting atop of rocky cliff edge, you can’t get more, New England than that.

Portland Head Lighthouse is a must-see destination when in the city.

Head along the Eastern Promenade for greenery and views of the boats heading in and out of the harbour.

Then pop down to East End Beach to play in the water and walk along the sand.

Commercial Street is not to be missed, with converted warehouses hosting independent shops, boutiques, cafes, and restaurants, it’s the perfect location for a spot of lunch or a coffee as you continue exploring.

Time from Boston: Under two hours.

19- Explore Kennebunkport, ME

Head north up the I-95 for 90 miles (144 km) and you’ll reach one of Maine’s little coastal towns, Kennebunkport, a popular summer destination among Mainers and out-of-staters.

Hit Gooch’s Beach, stroll along the sand, partake in water sports, and then walk from Gooch’s Beach through the town to Colony Beach to get a local feel.

Take the Parsons Way Trail for a gorgeous two-mile coastal walk passing by Spouting Rock and Blowing Cave, a great spot to watch the sun go down.

Time to Boston: 1 hour and 20 minutes. Book a day trip to Kennebunkport here.

Day Trips to New York

20- New York City, NY

Believe it or not, in just three and a half hours, you can be in the Big Apple. Admittedly, this is a little bit of a long drive for a day trip, but HELLO, it is New York City!

The only problem with this day trip is narrowing all your sightseeing activities to just one day.

Visit some must-see sites, like The Empire State Building, the Statue of Liberty and Brooklyn Bridge or shop till you drop in Soho.

Just make sure you don’t have too much fun, or you’ll miss your train back to Boston!

From Boston, head along the I-90 W and then on the CT-15 S, and you can be in NYC in 3 hours 40 minutes.

Alternatively, you can take the Amtrak Acela Express train for a more leisurely journey. The first train leaves Boston at 5.05 am and you’ll arrive in the big city by 8.30 am. Not bad!

Time to Boston: 3 hours 40 minutes. If you’re not game enough to drive or couldn’t be bothered to rush around, let someone else get you there and around on this day trip from Boston to New York City.