Your Ultimate Boston Summer Bucket List: 50 Things to Do in Boston & New England This Summer
By Steph Crawford | Steph Crawford Group | Boston Real Estate
Summer in Boston is something else entirely. The city transforms — the Esplanade fills up, the Harbor Islands come alive, the Public Garden is in full bloom, and every neighborhood from the South End to Beacon Hill has something going on. If you've ever wondered why people who live here never want to leave, summer is your answer.
Our team at Steph Crawford Group is deeply rooted in this city, and nobody captures the spirit of Boston living quite like our own Caroline Barry of @MakeBostonHome. This summer, she put together the ultimate Top 50 New England Summer Guide — and we're featuring it here because it's genuinely the only list you need from now through Labor Day.
👉 Access the full Top 50 Summer Guide here
Here's a taste of what's inside, broken down by category.
🚣 Classic Boston Activities You Have to Do At Least Once
Some things are classics for a reason. If you're new to Boston — or have been here for years and still haven't checked these off — this is your summer.
- Kayak or paddleboard the Charles River. There's no better way to see the city from a different angle. Rentals are easy to find and the views of the skyline are worth every paddle stroke.
- Swan Boat ride in the Public Garden. Yes, it's touristy. Do it anyway. It's Boston.
- Picnic in the Public Garden. Pack a cheese board, grab a blanket, and claim your patch of grass. One of the most civilized ways to spend a Saturday afternoon in this city.
- Stroll the Kelleher Rose Garden. Tucked inside the Back Bay Fens, this hidden gem is stunning in summer and almost always peaceful. A local favorite that most visitors miss entirely.
- Ferry to the Boston Harbor Islands. Georges Island, Spectacle Island, Peddocks Island — ferries run all summer and the day trips are completely underrated. Pack sunscreen and plan to stay awhile.
- Walk the Castle Island loop. A classic South Boston staple. The views of the harbor, the planes coming in low over the water, the smell of Sullivan's — it doesn't get more Boston than this.
⚾ Only in Boston
- Eat a Fenway Frank at a Red Sox game. Non-negotiable. Whatever your feelings about baseball, there is something about sitting in Fenway Park on a summer evening that makes everything feel right.
- Try golfing into Fenway Park. Yes, you read that correctly. It's exactly what it sounds like and it is absolutely worth doing.
- Seaport Sweat free outdoor workouts. The Seaport has become one of the most vibrant neighborhoods in the city, and the free fitness programming in summer makes it even better. Bring a friend.
- Visit one of the North End Feasts. Summer in the North End means street festivals, saints' processions, and some of the best food you'll find anywhere in New England. Check the schedule — these weekends fill up fast.
- Puppy Yoga. Because Boston summers call for it.
- Owl's Nest on the Esplanade. A warm evening, a drink in hand, the Charles River in front of you. Few places in the city feel more like summer than this.
- Treehouse Beers at the Pru. Pick up a four-pack (or six) of one of New England's most beloved craft beers without making the trek out to western Mass. The Pru location makes it dangerously convenient.
- Sam Adams Boston Brewery tour. A classic. Whether you've done it before or it's been a while, the Jamaica Plain brewery is a great summer afternoon.
🌿 Trail Walks & Green Spaces Around Greater Boston
Boston's green spaces and surrounding trail systems are genuinely world-class — and most people barely scratch the surface of what's available within an hour of the city.
- Middlesex Fells — Stoneham. Miles of wooded trails just north of the city. Great for a half-day hike without committing to a full road trip.
- Arnold Arboretum — Jamaica Plain. 281 acres of trees, plants, and winding paths, free and open year-round. In summer it's one of the most beautiful spots in the entire city.
- Garden in the Woods — Framingham. A native plant sanctuary that's worth the 45-minute drive west. Wildflowers, woodland gardens, and a pace of life that will reset your entire week.
- Maudslay State Park — Newburyport. If you haven't been to Newburyport yet, fix that immediately. Maudslay is a gorgeous trail system along the Merrimack River, and downtown Newburyport has some of the best restaurants and shops on the North Shore.
- Crystal Lake Beach — Newton. A swimming lake just 20 minutes from the city. A great alternative when you want water without the traffic to the Cape.
- deCordova Sculpture Park — Lincoln, MA. Sculpture, nature, and sweeping views of a reservoir — all wrapped into one extraordinary outdoor museum. A perfect Sunday.
🏨 New England Getaways Worth the Drive
One of the best things about living in Boston is what surrounds it. You're within two hours of some of the most beautiful coastline, countryside, and small towns in the country.
- The Rockport House — Cape Ann, MA (1 hour). Rockport is one of those towns that reminds you why you live in New England. The House is a beautiful base for exploring the Cape Ann coast.
- Chatham Inn — Cape Cod, MA (90 minutes). Classic Cape Cod charm with a polished edge. Chatham is the right end of the Cape — quieter, more refined, and worth every minute of the drive.
- Nantucket Inn — Nantucket, MA. If a full Nantucket trip feels like a stretch, the Nantucket Inn makes the island feel genuinely attainable. A long weekend there will remind you why everyone is obsessed.
- The Nevada Hotel — York, ME (70 minutes). Maine in the summer is non-negotiable, and York is the perfect entry point. Easy drive, beautiful beach, great restaurants.
- Harbor View Landing — Mystic, CT (2 hours). Head south for a change and spend a weekend in Mystic. The harbor, the lobster rolls, the Maritime Museum — it's one of the most underrated weekend trips from Boston.
- Walden Campervans. If you're feeling adventurous, rent a campervan and make your own itinerary. New England is made for road trips and this is the best way to do it.
The Full Guide
This is just a slice of what Caroline put together. The full Top 50 New England Summer Guide covers even more — more activities, more getaways, more reasons to love where you live.
And follow Caroline at @MakeBostonHome on Instagram — she posts consistently about what's happening in the city, neighborhood guides, and the kind of local knowledge that makes Boston feel like home.
Living in Boston This Summer
There's a reason people don't leave. The neighborhoods, the waterfront, the food, the culture, the green spaces — Boston in summer is the full picture of why this city commands the real estate prices it does.
If you've been thinking about buying or selling in Boston — whether it's a South End condo, a Beacon Hill penthouse, or anything in between — we'd love to talk. The market is active, peak season is right now, and we know these neighborhoods as well as anyone in the city.
📩 Reach out anytime: [email protected] 🌐 stephcrawfordgroup.com 📱 Follow us on Instagram: @stephcrawfordgroup
Steph Crawford Group is a luxury real estate team serving buyers and sellers across Greater Boston, specializing in the South End, Beacon Hill, Back Bay, and surrounding neighborhoods.
