Summer Weekend Trips from Boston

Boston is surrounded by natural beauty – there are lakes, mountains and/or the Ocean- practically in all directions; so it is a perfect starting point for weekend roadtrips.

Here are our favorite tried and true summer weekend destinations from Boston:

NORTH OF BOSTON DAYTRIP

A DAY trip might be the best weekend choice for many families.  With close ties to the South of Boston, we have not visited the North shore in a while and were happy to rediscover Massachusetts’ other Cape- Cape Ann and a nearby town of Ipswich on a recent day trip.  I will work on proposed day trip itinerary soon, but for now- check out Crane Estate and Hammond Castle, as well as the coastal towns of Rockport, Gloucester and Manchester-by-the-Sea.

Tip: Many beaches North of Boston are for residents only but you may want to plan a visit to a museum during the day  and coastal walk at sunset when parking fees are not collected.

THE BERKSHIRES 

(2-2.5 hours)

Update 2023 Tanglewood Music Festival and Jacob’s Pillow Dance Festival are back during summer 2023.

We come to the Berkshires every summer – for its magical air, natural beauty and exquisite art museums and historic estates (we enjoy it so much- we have NOT even skipped summer 2020: here is our updated Berkshires Picnics report from one of the recent summers).

And If you have not experienced Boston Symphony’s concert on the lawn of the Tanglewood Music Center in Lenox, MA — you have not fully experienced New England summer!  It is one event that could be both incredibly family-friendly and romantic!  For tips on how to attend Tanglewood concert with a family, I have made a youtube video:

 

(and this post).  For other kid-friendly activities in the Berkshires, read this story, and for the trip with or without the kids, my two-day Berkshires itinerary will give you lots of ideas to start planning your weekend escape.

Bonus idea: I have recently “accomplished” a recharge weekend escape to the Berkshires on my own- to the Kripalu Center for Yoga and Health.  Read about my “Anti-Yoga” Day at Kripalu here.

COASTAL MAINE

We recently updated our coastal Maine weekend itinerary- in search of best views and lobster rolls!

(1.5-2.5 hours depending on your itinerary)

The ocean water is colder, but there is an abundance of gorgeous coast line for admiring from land and sea.   We like the ocean walks in Ogunquit and York, and to experience waterfront city living and island day tripping – Portland is the place.  If you would like to combine it all in one weekend – with an added visit to a water park to praise your well-behaving kids, follow our summer weekend roadtrip through York, Old Orchard Beach and Portland here.

CAPE COD 

(1.5 hours to mid-Cape 2.5 hours to outer Cape, but consider summer traffic)

We love Cape Cod for camping, warm water swimming, National Seashore park, biking trails, main streets and the overall feeling of unassuming relaxation which reminds me of my childhood summers on the Black sea.  We are spending even more time than usual on Cape this summer 2020, exploring its diverse coastline. Check out our NEW post with our FAVORITE CAPE COD BEACHES. For things to do off the beach on Cape Cod, follow this article.

MARTHA VINEYARD 

(1.5 hours to the Cape, then an hour on the ferry)

Martha Vineyard is an island seven miles off the Southern coast of Cape Cod.  It is easier to day trip there if you are already spending time on the Cape (and are yearning for even more relaxation – island-style!), but in the past we have done day trips from our Boston suburb (you can catch a ferry from Falmouth and Hyannis on the Cape- follow this link for what to do on Martha Vineyard and how to get there details).

STOWE, VERMONT

 (3.5 hours)

Here is our trip report (with video!) from our recent family weekend in Stowe.

This is where the famous von Trapp family (whose story became the basis for the “Sounds of Music” movie) settled when they fled Austria to the United States in 1940.  You can still visit (or stay) in the historic Trapp Family Lodge and enjoy the vistas that reminded the family of their native Austrian rolling hills.   As you stay in the area find a hiking path to the falls, enjoy the scenic bike path, take a gondola ride up mount Mansfield, visit Ben and Jerry’s ice-cream factory, and stroll the main street and Lake Champlain promenade in the nearby Burlington.  Many years ago we spent the night at Grand Isle State Park campground – and enjoyed our own private beach access to Lake Champlain.

NEWPORT, RHODE ISLAND

 (1.5 hours)

Only slightly more than an hour away, Newport is an easy day trip from Boston.  We like to go boating in Newport Harbor (read our report here), walking the famous ocean Cliff Walk along the Gilded Age historic mansions (and visiting one of them- especially the Breakers), and touring around on a trolley bus.  We have recently discovered Castle Hill Inn for drinks on the lawn with water views.

 

NORTH CONWAY, NEW HAMPSHIRE

(3 hours)

New Hampshire is many families’ favorite summer lake escape.  We have also enjoyed our lake weekend on Long Pond, but our family’s “traditional” summer New Hampshire weekend outings have been to the Story Land amusement park in Glenn near North Conway.  If a two-day park visit leaves you wanting for more things to do, take a break at the Echo lake, climb Diana’s Falls, enjoy a train ride on Conway Scenic Railroad or just stroll the cute downtown of North Conway.

HERE ARE A LONGER TRIPS IDEAS (STILL DOABLE OVER A LONG WEEKEND):

COLLEGE TOURS IN THE NORTHEAST

If college touring is in your family plans this summer, be sure to check out College Touring to Upstate New York and Pennsylvania itinerary planning tips to make the college roadtripping enjoyable for the entire family.

HERSHEY, PENNSYLVANIA

(6 hours)

It is certainly one of the longer weekend trips we took, but I believe a visit to Hershey, Pennsylvania is worth it at least once- for chocolate, rides, and a fascinating history of this unique American corporate town.

NIAGARA FALLS, ONTARIO (WITH A SIDE TRIP TO TORONTO)

(7 hours)

is our longest (and newest) weekend roadtrip from Boston! This post on Niagara Falls weekend not only provides the usual useful details (and awesome photos from the blog photographer Vit), it has not one but two! 20-second videos highlighting our Toronto and Niagara experiences (for full size videos, be sure to visit our NEW Family Travel YOUTUBE channel!

COUPLES WEEKEND: Bromont, CANADA

Summer 2022: Canadian borders are open for roadtripping from the US and we have repeated this Spa Trip in May 2002 (minus the Harvest Fest which is happening in September)

(4.5-5 hours)

The drive to Bromont-Magog takes a little longer than three hours (4- 4.5), but it will take you to another country (Canada), where they speak a foreign language (French) and have a rich spa tradition (Nordic).  Follow us on our weekend couple’s escape to Magog in the province of Quebec.

Bonus Idea: if you love spas, our Spa Hopping in Eastern Townships (just over the border) will come handy (and if you think you don’t- you’ve gotta try!)

MONTREAL CANADA

(6 hours)

For a long weekend, you can certainly venture to Montreal, Canada, the most European North American city. Here is our list of Top 10 Montreal.

and if visiting Olympic sites is in your heart, a trip to LAKE PLACID, NY is a must (6 hour-drive).

What is your summer favorite weekend trip from Boston?

 

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