Our 2015 Year of Weekend Celebrations in Pictures

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:


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.

roadtrips from boston
Crane Estate in Ipswich.


(2-2.5 hours)

Update for summer 2024 Tanglewood Music Festival and Jacob’s Pillow Dance Festival schedules.

Our 2015 Year of Weekend Celebrations in Pictures
The view onto the Berkshires Mountains from Naumkeag Estate in Stockbridge, MA

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 Culture Picnics report and recent summer visit post about Three Concerts in one weekend with Teens.

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.

Tanglewood summer


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)

Road tripping Coastal Maine with Kids.
Cliff Walk, York

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.

Road tripping Coastal Maine with Kids.
Peak Island is only 15-minutes ferry ride from Portland, Maine but feels so island-like and remote


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

April School Vacation 2017
Marconi Beach. National Seashore, Cape Cod

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.


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

Read the very fresh off the boat account of our recent day trip to Nantucket.


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

Family vacationers visit Martha Vineyard on a day trip from Hyannis, Cape Cod
Aquinnah Cliffs, Martha Vineyard

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).


 (3.5 hours)

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


Summer Weekend in Stowe Vermont
Viewpoint Frenchman’s Pile, Mount Mansfield Vermont

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.

Our campsite on Lake Champlain, Stowe, Vermont


 (1.5 hours)

Family Sail in Newport Harbor, RI
Sailing in Newport Harbor, Rhode Island

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.



(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.

12+ Fall Weekend To Do Ideas in New England
Storyland Park in Glenn, HN offers low-key rides for young kids and mountain vistas for parents



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.

Wine tasting in Finger Lakes after a day of college touring- it is even more beautiful in the summer!


(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.

Roadtrip to Hershey, Pennsylvania, from Boston
Chocolate making at Hershey, Pennsylvania


(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!


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)

Spa Nordic Station, Magog, Canada

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!)


(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.

Our favorite things to do on a long weekend escape to Montreal- with or without kids
Old City 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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10 thoughts on “Summer Weekend Trips from Boston”

  1. These all look fab! I would love to explore the East Coast more. I’ve lived in the Midwest, West Coast and now Southwest – I haven’t had a chance to explore Eastern destinations much.

  2. You live in a really beautiful city, Victoria. Not only you have access to arts and culture in Boston, but you are also within a short driving distance from a lot of exciting places, like Magog, Canada. I’d love to explore the East Coast more, but for me it’s a 6 hours trip by plane. Not easy to do in a week-end.

  3. So many incredible places within reach of Boston! I’ve only done the Berkshires, Cape Cod and Stowe from this list, all of which I adored. Noting the others for the future, though – New England is somewhere I cannot wait to get back to.

  4. So many wonderful places so near Boston. I’d choose Cape Cod, Martha’s Vineyard, Rhode Island and the Ben and Jerry’s Factory!

  5. Several of these spots are on my list of weekend trips to do from NYC. I really want to go to Martha’s Vineyard and Cape Code. I guess the other idea I would add to your list is Block Island. It is just so peaceful! Thanks for sharing on #TheWeeklyPostcard.

  6. Thanks for the ideas – we have a cruise that ends in Boston during 2019 and are planning on driving up to Canada with some stops along the way. You’ve given us some starting points as we begin to plan!

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