What To Do in Boston in August

Isn't this weather just divine? Some of you guys have summer Fridays, but all of you are probably enjoying the longer days of sunshine! Are you planning a trip to Boston in August? Are you looking for a Boston vacation or staycation in August? Year-round, Massachusetts is a great vacation spot for domestic and international tourists alike. Late nights and walking adventures abound in August, and we are excited to share some memories.

Here are some ideas on how to enjoy a Boston Vacation or Boston Staycation in August:
What To Do in Boston in August


Free Outdoor Shakespeare in the Park


Every year we show up early around 6pm to see Shakespeare in the Park for free on Boston Common. When they open the rope, we rush to the front by the stage and steal the best seats of the show. You can bring a yummy picnic and while they don’t let you bring your own tall chairs, those little foldable mountain chairs are perfect for the occasion. Commonwealth Shakespeare Company performs the show every day but Monday but check the weather to see if it’s still on.



Take a Food Tour or Chocolate Tour with Off The Beaten Path Food Tours


We run our Food Tours and Chocolate Tours year-round and our friendly guides can’t want to meet you! Our Union Square Food Tour is a new addition to the calendar, and we have lots of stories to share about the neighborhood foodie haven. So check the Tour Calendar for something fun going on this week.



Dine Al Fresco or Gather Lunch At Various Farmers Markets


Here’s our list of the best Outdoor Dining in Boston. Want a picnic lunch instead? In all of the neighborhoods that we tour, there is a local farmers market. Check out this aggregator to find the Massachusetts Farmers Market near you!



Cheer on the Red Sox and sit near the Lone Red Seat!


Food and sports go hand in hand, we think you’ll agree. Our Fenway Food Tour which explores the best and most iconic eats in this historical neighborhood that’s now a foodie hotspot. We love this new tour, full of American Ballpark eats! Check out our post of our Favorite Boston Sports Bars, and catch the game after one of our tours this weekend.



Smell the Roses


In Brookline, MA you can rent a Bird electric scooter and scoot your way around the city. You can also rent an electric bicycle to help you up the hills in nearby Somerville. Some of our favorite places to walk around and enjoy nature include:

  • The Fens
  • Minuteman Bike Path – Somerville to Bedford, MA
  • Jamaica Pond
  • Boston College/Chestnut Hill Reservoir
  • Fresh Pond in Cambridge, MA
  • Charles River in Cambridge, MA (Sundays closed to vehicles)


You can pick the most gorgeous flower bouquets straight from the field at Parlee Farms which is a 30 minute drive north!

For fruit picking, we recommend the most delicious nectarines at Carlson Orchards in Harvard, MA.



Try A Bar Crawl with our Craft Breweries


Check out our blog post about our favorite craft breweries in Boston. There’s so much creativity in the Boston brew scene, from the label to the process/recipes to the names of the local bottles, these are truly labors of love. On our tours we often sample beer, and you can email us for specific recommendations if you want more recommendations.



Make It a Bubble Tea Date or Late Night Dessert


Check out our list of our Favorite Bubble Tea in Boston. From avocado shakes to unique frozen creations, you won’t want to miss these fun and inventive spots. Dessert more your thing? Our Chocolate Tours are a perfect adventure or check out our Most Indulgent Desserts in Boston.



Enjoy Music or Theater including Live Shows and Movies


Lift your spirits with a performance that wows. There are so many awesome music venues in Boston, from outdoor to indoor beats! Check out our list of our favorite music venues in Boston. Year after year, we love the free movies at the Hatch Shell (Friday Flicks). On August 26, 2022 they are showing Cruella at the Hatch Shell on the Esplanade. On August 19, 2022 Boston Harbor Hotel is showing “Encanto” (and grab a 7:45pm dinner reservation at the Rowes Wharf Sea Grille to get the best seat by the pier!)



Plan a Bachelor or Bachelorette Party: A Food or Chocolate Tour!


It’s “wedding season” and our Food Tours and Chocolate Tours make perfect bachelor or bachelorette parties. We’ll create some special surprises at each stop. Contact us to find out more.



The Usual: Art Galleries, Restaurants, Historical Sites are all open


Check out some of our other recs of things to do in Boston like this blog post on Off The Beaten Path Things To Do in Boston. Enjoy our city and explore all of its off the beaten path finds.

Our Food Tours and Chocolate Tours of interesting Boston neighborhoods are a can’t-miss August activity in Boston. So whether you’re a local or tourist, start practicing saying “wicked cool” and check our Tour Calendar for what’s going on this week.

Share this post:

If you like this post, you'll love

browse the blog
Browse by category
Also See...