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15 Things to Do in Boston This Summer

15 Things to Do in Boston This Summer

Boston is a different city when summer rolls around. The sun is shining, many of the students have scattered (and those who remain are not under as much pressure), couples lie in the grass, friends listen to live music while dining al fresco, and people are friendlier and happier on the whole. Boston is kind of like the serious student who, surprise, surprise, actually likes to relax and enjoy a party as much as the next guy.

While I’m spending my summer months this year in the lovable heat trap that is Manhattan, I have my fair share of happy memories of summertime in Boston, and I’m sharing 15 of my favorite activities with you to help you make some happy memories of your own.

1. Wander the Arnold Arboretum

Designed by Frederick Law Olmsted, the Arnold Arboretum is among the very best Boston has to offer. Paths easy for walking or biking wind through hundreds of acres of forests, brooks, gardens, and manicured fields. A great place for a stroll, a ride, a picnic, or a run with your puppy.

2. Kayak on the Charles

Kayaking on the Charles River is a wonderful way to enjoy Boston and Cambridge from a novel angle. Paddle through light waves and enjoy views of the Boston skyline and the Harvard and MIT campuses. $20 per hour for a two-person kayak at Charles River Canoe & Kayak.

3. Dine in Roslindale’s European courtyard

I’m originally from Roslindale, a lovely neighborhood in Boston that a lot of people haven’t heard of. While the list of things to do in the heavily residential area hardly stretches on for miles, hidden in Roslindale Square you’ll find a lovely, lively European courtyard with twinkling lights, brick arches, and stucco walls.

The space is shared by three restaurants, a wine shop, and a cheese shop. On a gorgeous evening, you’ll always find happy crowds of families, couples, and sometimes even dogs. Birch Street Bistro and Village Sushi and Grill are my personal courtyard favorites.

4. Fly a kite at Castle Island

Castle Island, located in South Boston, is the best place within the city to enjoy the ocean. Go on a long walk across break walls, wander around the old military fort, fly a kite (It’s always windy.), or get in the daunting but improbably fast line at Sullivan’s for very reasonably priced beach food like fried clams, hot dogs and soft serve.

5. Explore Forest Hill Cemetery

Forest Hills Cemetery may be the single most under appreciated spot in all of Boston. Yes, it is a cemetery, but it is also a lush arboretum and New England’s largest outdoor sculpture garden. Its rolling 275 acres are home to a beautiful pond, Tiffany stained glass, bike paths, and exquisite memorials from the Victorian period onward, including a breathtaking monument by D.C. French (sculptor of the Lincoln Memorial).

Forest Hills is a good place to explore by bike or by foot with someone you’d like to contemplate life’s larger questions with.

6. Go boating on Jamaica Pond

Jamaica Pond is a beautiful place to rent a rowboat, sailboat, or kayak for an hour or two. When you come back to shore, stroll over to Centre Street for ice cream at J.P. Licks, artisan bread at When Pigs Fly, tapas at Tres Gatos, or thrift shopping at Goodwill and Boomerang.

7. Swim in Mirabella Pool

The North End’s “Italian Riviera,” Mirabella Pool is one of Boston’s best hidden gems. This pristine Olympic-length pool is tucked right inside Boston Harbor, so you can watch the ocean waves lapping as you do your own laps.

When you work up an appetite, enjoy one of the snacks or sandwiches on sale for $1-3, or explore the surrounding Italian neighborhood to find something certainly delicious.

8. Order an affogato at Caffe Paradiso

Caffe Paradiso, a classic old Italian cafe festooned with World Cup paraphernalia, is the perfect place to people-watch and to enjoy a gentle breeze. The North End cafe opens its entire storefront when the weather is nice. Their affogato—vanilla gelato drowned in a shot of espresso—is a delightful treat.

9. Enjoy the views from Custom House Tower

A stone’s throw from the harbor, the Custom House Tower allows the public onto its 20th-floor open-air observation deck for $4 per person at 2 pm, Mondays through Thursdays, according to the most recent article I could find. Because the deck’s information is not widely publicized, I would recommend calling ahead when planning your visit to confirm its current operating schedule: (617) 310-6300.

10. Picnic at Christopher Columbus Park

With vine-covered arches and views of ships coming in and out of the harbor, Christopher Columbus Park — despite its dubious man of honor — is one of the loveliest spots in the city to enjoy a romantic picnic.

11. Take a cruise to the Harbor Islands

Skip over from Christopher Columbus Park to the boarding dock for the Boston Harbor Islands, which open to the public during the summer. With great views and opportunities for hiking and snacking, the islands are a fun way to enjoy Boston’s coastal position, and nothing says summer like a windy boat ride.

12. Ride the Swan Boats

While Boston has its fair share of tourist traps (e.g. Quincy Market), the Swan Boats are definitely not one of them. Dating back to 1877, the Swan Boats cost $3.50 per person and are one of the most charming ways to enjoy the sunshine.

13. Pick up gourmet goodies at the Copley Square Farmers’ Market

The Copley Square Farmers’ Market is a lovely place to fill up a tote with fresh produce, flowers, pastries, candied nuts, and more before continuing on a longer downtown adventure or going for a picnic.

14. Soak up some free culture at Shakespeare on the Common

The Commonwealth Shakespeare Company will present free performances of Love’s Labour’s Lost every night from July 20 to August 7 on a large stage set up in the center of the Boston Common.

15. Seize the weekend getaway!

As you may have noticed by now, I am a big fan of maximizing the weekends as a time for travel, often leaving town after work or school on Fridays. The Northeast U.S. is a gorgeous place to be in the summertime, and being in Boston positions you for an unbelievable wealth of day- and weekend trips. Try some of the following, ordered by driving time, and let me know in the comments if you need any advice while planning your trips!


  • Sharon, MA (30 minutes)
  • Walden Pond, MA (30 minutes)
  • Drumlin Farm, MA (45 minutes)
  • Nantasket Beach, MA (45 minutes)
  • Cohasset, MA (1 hour)
  • Hammond Castle, MA (1 hour)
  • Newport, RI (1.5 hours)
  • Cape Cod, MA (2 hours)
  • White Mountains, NH (2.5 hours)
  • Martha’s Vineyard, MA (2.5 hours)
  • The Berkshires, MA (2.5 hours)
  • Burlington, VT (3.5 hours)
  • Hudson River Valley, NY (3.5 hours)
  • New York, NY (4 hours)
  • Bar Harbor, ME (6 hours)

1 Comment

  1. 4 years ago

    Love this list and your Boston guide! Copley Square Farmers’ Market is amazing 🙂 I definitely need to do more exploring when I’m back in Boston. Thanks for the tips!!