15 Best Day Trips from Boston - The Crazy Tourist

As one of the oldest cities in the United States of America, Boston has a whole host of history and culture to explore.

Being set in Massachusetts means that Boston is only a stone’s throw away from some of the East Coast’s most impressive scenery and historically significant settlements.

Once you have had your fill of the busy streets of Boston there are plenty of day trips from the Massachusetts capital that will keep your wanderlust activated and your sense of adventure fulfilled.

Let’s take a look at the best day trips from Boston:

1. New York

Quite possibly the most iconic city in the world, New York is only a few hours away, by drive, from Boston.

In the space of a day you can tick off all the major bucket list sights and landmarks in New York with enjoyment and ease.

Spend the morning exploring the Statue of Liberty and the Empire State Building, catch lunch at the Hard Rock Cafe perhaps and laze the afternoon away in Central Park.

Before you hit the road once more, after dark be sure to take a wander through the wonderland that is Time Square.

Come rain or shine, a day in New York is always memorable.

2. Newport

Set on Aquidneck Island Newport is a city lying in New England State.

This rustic city is home to the great and the good and has some of Rhode Island’s most opulent homes.

Should you take a stroll down Bellevue Avenue you’ll see the famous Gilded Age mansions that line this affluent street.

Many of these are now museums offering fascinating insights of this historic area.

A visit to The Breakers mansion and Marble House are the architectural highlights of a day trip to Newport.

The International Tennis Hall of Fame can also be found in Newport and was the home of the first ever U.S Open Championship 1881.

3. Plymouth

Plymouth Rock holds huge significance to Massachusetts for it marks the site in which William Bradford disembarked from the Mayflower and founded the Plymouth Colony way back in 1620. Plymouth Harbour is a particularly photogenic harbour that to this day is the home of The Mayflower II. Marine history enthusiasts will be thrilled to visit such an impressive ship.

From Plymouth is it possible to visit the Monument to Our Forefathers also known as the Pilgrim Monument and is the largest freestanding granite monument in the world.

A visit to Plymouth is the perfect way to expand your knowledge of modern American history.

4. Cape Cod

Cape Cod is an incredibly popular holiday destination for locals and international visitors alike.

Home to quaint Massachusetts villages, seafood cafes and as well as rugged and picturesque coastline, Cape Cod is a must-visit.

Cape Cod’s oldest village, called Sandwich, is a real highlight.

The Heritage Museum and Gardens to make for a wonderful addition to a day trip from Boston, especially during the summer months when the flowers are in bloom.

Even in the winter months a trip to Cape Cod is inspiring.

Nothing like a blustery beach walk to blow the city smoke away.

5. Martha’s Vineyard

Lying to the south of Cape Cod Martha’s Vineyard is the long standing New England summer colony that has plenty to explore.

Best accessed by boat, the ferry from Falmouth to Martha’s Vineyard takes just 35-minutes.

Once firmly on the land again you can visit the gorgeous gingerbread cottages in Oak Bluffs.

Edgartown is another must-visit town on Martha’s Vineyard and is known for its whaling captain homes and of course plenty of gift shops too.

In the later afternoon ensure to make time to visit Aquinnah and the Gay Head Cliffs.

The lighthouse is practically regal in its presence.

6. Salem & Marblehead

Away from all the modern history of New England lies an intriguing, older history of another kind.

Salem played host to the Witch Trials of the 1600s and to this day are visited by the spiritually curious from around the world.

In addition to details about the Witch Trials during a trip to Marblehead it is possible to brush up on your Naval history for Marblehead is the birthplace of the modern American Navy.

While in town be sure to visit Abbott Hall to observe the famous oil painting ‘The Spirit of ’76’ by Yankee Doodle.

7. Plimoth Plantation

Founded in 1947 Plimoth Plantation is a living history museum that makes for a fascinating and truly enjoyable day trip from Boston for all the family.

Walk in the footsteps of the pilgrims and learn about how this colony was created.

Taking elements of village life in 17th Century England Plimoth Plantation features the Town Brook where a water-powered grist mill still grinds away.

A day trip to Plimoth Plantation can be teamed with a visit to Cole’s Hill, The National Monument of the Forefathers and Plymouth Rock for a full and informative experience.

8. Good Harbor Beach

If a seaside day is in order then a visit to Gloucester’s Good Harbor Beach is a great decision.

With soft white sand and cool Atlantic ocean tides Good Harbor Beach has something for everyone.

If you’re brave enough to swim in the cold sea then go ahead.

There is a team of lifeguards on duty throughout the summer months.

Boogie boarding and skimboarding are popular pastimes at this beach.

On low tide it is possible to walk through the shallows out to Salt Island.

There are plenty of restaurants and cafes around Good Harbor Beach but feel free to bring a picnic, just take your rubbish home with you.

9. Provincetown

Provincetown, Massachusetts — Provincetown

If you really want to enjoy all that Cape Cod has to offer then a visit to Provincetown will be just the ticket.

Located at the northernmost hooked tip of Cape Cod Provincetown, affectionately called P-Town has been the long-standing hangout for artists, musicians and the LGBTQ+ community.

Home to dozens of art galleries, edgy nightclubs and plenty of speciality shops too Provincetown is has a modern outlook with a traditional backdrop.

Commercial Street is where the action is at and in the summer months is practically buzzing with holidaymakers and locals alike.

10. Castle Hill

Located on the Crane Estate, Castle Hill is a breathtaking coastal mansion set in the most impeccably maintained gardens and grounds.

With 59-rooms Castle Hill was designed by David Alder, a world renowned architect.

An easy going, even romantic day out to Castle Hill is achievable from Boston for it is merely 55-minutes away from the city centre.

It is possible to opt onto a guided tour of Castle Hill, however, should you wish to take the day at your own pace you are more than welcome to explore this magical grounds without a guide.

Throughout the day you’ll likely spot deer in the estate and migrating birds too.

11. Glendale Falls

If you want to take time out, away from the city, the best pace to reconnect with nature is Glendale Falls.

Both the longest and the strongest series of waterfalls in all of Massachusetts, Glendale Falls are a real spectacle.

Making for a relaxing and peaceful day trip from Boston walking through the scenic routes leading to Glendale Falls you’ll pass hemlock and birch trees, shadbush, maple and beech too.

A truly versatile and natural area of Massachusetts, a trip to Glendale Falls is both inspiring and grounding.

Free to enter, Glendale Falls is perfect for travellers on a budget.

12. Naismith Memorial Basketball Hall of Fame

Sport enthusiasts will have the Naismith Memorial Basketball Hall of Fame already high on their bucket list for Boston.

Featuring over 300 world famous and game changing players, the Hall of Fame is home to all kinds of memorabilia and artefacts.

Over 40,000 square-foot in size the Naismith Memorial Basketball Hall of Fame is the largest of its kind.

If you want to stock up on your basketball kit, memorabilia or even just novelty items the Hall of Fame store is a sporting wonderland just waiting to be explored.

Suffice to say, you won’t leave empty handed.

13. Wrentham Village

Why pay city prices when you can head to Wrentham Village and get premium brands for high street prices.

For travellers with cash to splash a visit to Wrentham Village Premium Outlets is the perfect way to spend a day away from Boston.

With men’s, women’s and children’s brands all on offer Wrentham Village is another place where you won’t leave empty handed.

Offering up to 65% off leading luxury brands Wrentham Village offers a touch of the high-life, how the other half live as it were.

There are a number of great restaurants and cafes at the outlet centre that provide a welcome respite from the dressing rooms.

14. Castle Island Park

Not really an island at all anymore, Castle Island Park is home to Fort Independence.

Built on reclaimed land Castle Island Park has been connected to the mainland since 1928. Guided tours of Fort Independence run every Saturday and Sunday between 12 pm and 3.30 pm and are very informative.

After the tour is over head over to Carson Beach and grab a bite to eat at Sullivan’s cafe.

They do great bagels and lobster rolls.

It is possible to visit both Castle Island and the less crowded George Island in one day.

To access George’s Island you must hop on the shuttle ferry.

15. Rockport

Home to only 7,000 year-round residents Rockport is a classic New England town that lies in Cape Ann.

With the Atlantic Ocean hitting the town’s perimeters on three sides there is a coastal charm to Rockport reminiscent of a small Cornish fishing village.

Home to mostly artists and fishing families Rockport has a small town feel and is set up perfectly for the day tripper.

With plenty of locally run cafes and fresh seafood restaurants on offer many visitors find themselves hopping from one eatery to another before a short coast stroll and drive back to Boston.