If you are planning a road trip from southern New England, Boston can be a perfect base as it is centrally located. You can get a hotel and then take many great day trips from Boston to experience the best that this area has to offer.
You will want to start by taking a few days to experience New England’s largest city’s feel. You can read my guide for One Day in Boston with Kids (still a good overview even for adults). Also, be sure to check out my list of hikes right around Boston.
Short Day Trips from Boston
These day trips from Boston are around an hour’s drive from Boston.
Salem, Massachusetts
Witch City, USA, also has a fantastic art museum and Hawthorne’s House of the Seven Gables. Read on for how to spend a day in Salem.
Fall River and New Bedford, Massachusetts
This center of fishing life in colonial New England is now predominately Portuguese. You can visit the New Bedford Whaling Museum, the church that was part of Herman Melville’s Moby-Dick inspiration, and the Lizzie Bordon House. Read more about the area in Haunted New England.
Rockport, Massachusetts
Spend a day exploring this picture-perfect fishing village on the coast north of Boston.
Cape Cod, Massachusetts
There is a lot to explore on this peninsula south of Boston, but you can explore the upper Cape in one day from Boston. Most of my exploration of the Cape has been by bicycle.
Portland, Maine
This foodie town also has lighthouses and parks to explore. Check out 47 Cool Things to Do in Portland, Maine.
Providence, Rhode Island
The capital of Rhode Island has canals to stroll along, great restaurants, and art museums. Read on for The Best Things to Do in Providence.
Newport, Rhode Island
This colonial town on Aquidneck Island has excellent beaches, hiking, dining, and a lot of history. Explore A Local’s Guide to Newport.
Sutton, Massachusetts
Hike this trail along the base of the 75-foot rock Purgatory Chasm and get ice cream at the farm next door. Read more about a day at Purgatory Chasm.
Concord, Massachusetts
Concord was not only an important location in the American Revolution but also in American Literature. Walden Pond sits in Concord, as well as Louisa May Walcott’s home. Read my itinerary for one day in Concord, Massachusetts.
Plymouth, Massachusetts
Visit the recreation of the Native American and pilgrim colony following the landing at Plymouth Rock.
New Bedford, Massachusetts
Explore the colonial whaling capital of the world, located on the southern coast of Massachusetts. This area also has a large Portuguese population, a fort, and was a stop on the Underground Railroad.
Read about how to spend a day in New Bedford.
Whole Day Trips from Boston
It will take about 2 hours to get to these full-day trips from Boston.
Martha’s Vineyard
Sand dunes, farms, Kennedy history, and gingerbread cottages, this island off the coast of Massachusetts will introduce you to the best New England has to offer. Read on for Things to Do in Martha’s Vineyard.
Woodstock, Vermont
Woodstock is sometimes known as the quintessential New England town. It is nestled in Vermont’s Green Mountains and alive with the state’s art culture. Plan your day with Things to Do in Woodstock, Vermont.
Northampton, Massachusetts
This arty town in northwest Massachusetts is the home of Smith College. Read on for how to spend a day in Northampton.
The Berkshires, Massachusetts
One of the most transcendent concerts you can experience will take place at Tanglewood in the rural mountains of western Massachusett. The Berkshires give ample opportunities for hiking, leaf-peeping, and exploring small New England towns.
New Hampshire’s White Mountains
Take a foliage drive or go waterfall hunting through the White Mountains.
Mystic, Connecticut
Explore the seaport at this colonial town on the Mystic River. Investigate more things to do in Mystic.
Mount Major, New Hampshire
The views from the peak of this half-day hike are incredible. You will see New Hampshire’s lakes and highest peak, Mount Washington, in the distance. Learn more about climbing Mount Major.
Shelburne Falls, Massachusetts
This village nestled in the Berkshire Mountains has the Bridge of Flowers, a waterfall, glacial potholes and an art-filled downtown. Read about how to spend a full day in Shelburne Falls.
Which day trips around Boston have you taken? Which are the highest on your list? Please let me know if you have any questions in the comments.
I love this list! Boston is such a cool city and I love the idea of spending more time there and venturing out so this list is so helpful!
So many great day trip options from this city! Nice when there is that option, for travellers, it means you can extend your holiday. Make Boston your home base and see some of those smaller towns you have listed. I would love to see more of the nature, in New Hampshire, like Mount Major or Massachusetts with Martha’s Vineyard.
Such great day trip plans even a month of stay there will not suffice to experience it all! The short day trips really sound good and doable. I have not been to Boston yet, but hopefully I will some day with this helpful post! Great pic to go with the post.
Wow! So many things to do. It would really be worthwhile to make Boston a base for a week and do these trips to immerse yourself in the region.
Visiting the east coast has always been something i’ve wanted to do. I’ve seen Boston & DC but that’s about it! Rhode Island, Connecticut, Vermont, Main, I want to see them all!
Funny enough I’ve heard most of these day trips destinations from Boston although I don’t know their locations to Boston. I would like to visit most of them, but I think Fall be the best time?
Some of the locations are close enough for a day trip but would plan an early start in the day because even though they are close enough for a day trip, traffic can play a big factor especially during rush hours… planning a trip to the South Shore or Cape Cod offers only 2 travel lanes for most of the trip once you are on Route 3 which starts in Braintree which is about 9 miles south of Boston and the from Braintree to the beginning of the cape it’s about 45 miles or so… I mention this trip because I am very familiar with this section of MA and I live in Plymouth which is about 10 miles from Cape Cod… The Fall or Spring would be best as far as traffic to the cape but many places close down from Oct to Apr because many businesses depend on tourists during the Summer.
You are right about Boston traffic being a bugger. It is always best to consult Google traffic before leaving, start early or consider public transport. I love travelling in shoulder season.
While there’s still so much to see and do on my actual Boston list, I *did* take a day trip from Boston during one of my visits. We followed your recommendation to visit Providence, RI, and had a lovely day!
I just love the northeast and you’ve given me even more places to explore up there! Perfect fall long weekends!!!
Cape Cod, Massachusetts would be my #1 choice. Haven’t been since I was little and have such fond memories!
I have been to Boston several times now and even took a trip up to Maine & Connecticut once but I have been quite lax on visiting the other areas. For me, I really want to see more of the New England Coastal areas like Providence and I know Darcee would love to see Martha’s Vineyard!