Welcome back to The Abroad Blog! If you’re new here — thanks for stumbling upon my little corner of the internet! If you keep up, you would know that my most recent posts have recapped some of my weekend trips so far in 2023, including Sarasota, the Route 30A road trip I took back in December, and lots of Charleston content, as I’m approaching two full years living here! I’m also still chipping away at tons of travel guides for Europe. In the meantime, I’m pivoting back to a core content pillar on my site – New England! I was born & raised in Boston and spent 23 years of my life exploring as much of New England as I could before packing up my life and moving down to Charleston, SC for grad school. In preparation for months of adventure up north, today’s blog post is going to focus on the best things to do in Boston during the summer. Plus, a few bonus suggestions for other areas of Massachusetts!
Disclaimer: This blog post is in collaboration with Camp Wylo. Camp Wylo is a weekend getaway for adults aged 21+ taking place in the beautiful Berkshires of Massachusetts this June. While I’ve not yet attended the camp myself (this is their first year!), I love the idea and was more than happy to plug the camp in this blog post about things to do in Greater Boston during the summer. As always, all opinions written here are my own. Continue scrolling to the end of this post for more information about the camp!
Fenway / Kenmore
Boston is a small city, but I’m going to break this post up by neighborhood! If you’re looking for more of a New England bucket list, this post covers ideas for the entire state of Massachusetts, in addition to New Hampshire, Vermont, Maine, Connecticut, and Rhode Island for all 4 seasons! First up, the Fenway area.
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Go to a Red Sox Game
This is my top recommendation for this area, and one of my top recommendations for the entire city of Boston for best things to do during the summer. Fenway Park is the oldest still in use MLB stadium in the US. It opened in 1912 and has some of the most unique and fun traditions. Whether you’re a baseball fan or not, check out a game for the 7th inning stretch, Sweet Caroline sing-along, and of course — a Fenway Frank.
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See a concert at Fenway
Not a baseball fan but still want to experience the park? Check out Fenway’s concert schedule! Each summer, Fenway hosts a series of big artists in Boston! The atmosphere here on a warm summer night is just unbeatable — especially if you’re a country music fan. Zac Brown Band here is a MUST!
Pro-tip: The other two popular concert venues in Greater Boston area are the Xfinity Center in Mansfield and Gillette Stadium in Foxborough. Gillette is the largest, so if you’re interested in seeing superstars like Taylor Swift of Kenny Chesney, look there!
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Bar hop on Lansdowne Street
Lansdowne Street is one of the many roads just outside of Fenway Park and is home to some of Boston’s best bars. This area gets packed after a game or concert but is a great time! Check out Lansdowne Pub, Cheeky Monkey, and my personal fav — Loretta’s.
Pro-tip: Yawkey Way is another famous street in this area. It’s a popular place to grab a drink or bite to eat before a game too.
Beacon Hill / Back Bay
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Stroll down Charles Ave.
Beacon Hill is one of my favorite neighborhoods in Boston. It’s so historic, has so much charm, and is totally walkable. This neighborhood is smaller compared to others, but don’t miss Charles Ave! Stretching from the Charles River and the historic Liberty Hotel (which used to be a jail, by the way), all the way to the Boston Common, this street is full of shops and restaurants.
Pro-tip: Be sure to visit the new Beacon Hill Bookstore. This charming bookstore is tucked away on Charles Ave and has a sweet café inside!
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Have a picnic in the Boston Common & Public Garden
The Boston Common is the oldest public park in the US and is one of the most historically significant. It sits adjacent to the Public Garden, which is my favorite park in the city. Grab a blanket here and some food to enjoy a picnic by the pond.
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Walk the Freedom Trail
The start of the 4-mile-long Freedom Trail is at the Boston Common Visitors Center. This Visitors Center has restrooms, free maps, and is the perfect place to begin your adventure through historic downtown Boston.
Fun fact: I used to be a tour guide on the Freedom Trail! While I’m not guiding tours here at the moment, I do have several blog posts covering tips for you.
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Ride a Swan Boat
Riding a swan boat in the Public Garden is such a quintessential New England activity and is one of the best things to do in Boston during the summer. These swan boats have been run by the same family since the 1870s and still brings joy to thousands of boaters each summer. I have such fond memories of doing this as a little girl, and highly recommend this activity for you and your family too.
Pro-tip: A ticket to ride costs less than $5!
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Shop on Newbury Street
Shopping on Newbury Street can be enjoyed year-round (this is both a blessing and a curse), but Newbury really comes to life during the summer months. During a nice day, Bostonians can be found here taking advantage of the outdoor dining that lines this street. My personal fav? Stephanie’s on Newbury.
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Enjoy the Esplanade
The Esplanade runs down the side of the Charles River for 3 miles from the Museum of Science to Boston University. Here you’ll find roller-skaters, walkers, runners, and everything in between during the summer months; along with concert go-ers at the Hatch Shell and beer enthusiasts at Night Shift Brewing.
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Rent kayaks or a sailboat at Community Boating
Also located along the Esplanade is the Community Boating center, which offers sailing camps for young children and rentals for people to try! My company, EF Education First, has hot pink branded kayaks and sailboats here (a genius PR move, if you ask me), so keep an eye out!
North End
The North End is Boston’s Italian neighborhood, which really comes to life during the summer months.
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Eat on Hanover Street
During a warm weekend, eating dinner on Hanover Street is one of the best things to do in Boston during the summer. Each Italian restaurant here spills out onto the sidewalks for additional, al fresco dining — bringing the smells of garlic, pesto, and freshly baked focaccia along with it.
My favorite restaurant here is Trattoria il Panino. They serve all their homemade pasta dishes in pans. So fun. And so delicious! I also love Quattro for its pizza and pretty much every spot for an espresso martini. Boston is known for its espresso martinis.
Be sure to grab something sweet at Mike’s Pastry here too! There’s a huge rivalry between Mikes Pastry and Modern Pastry – both have been family-owned since the early 1900s and sit diagonally from one another on Hanover Street. Most people in Boston have a personal preference, and mine is definitely Mike’s!
Seaport District
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Day drink at Cisco Brewers
Cisco Brewers has a pop-up in the Seaport that is SO FUN! This area is perfect for day drinking and will stay lively well into a warm summer night. There are a few different bars in this area, selling all types of beer, wine, and frose options. There’s some food too. I recommend hanging out here for a while after work or on the weekends during the summer months.
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Eat at the Barking Crab
The Barking Crab seafood restaurant is another quintessential New England spot. Grabbing a seafood dinner here is one of the best things to do in Boston during the summer months. Plus, Boston is known for its seafood so be sure to try some clam chowder or a lobster roll here.
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Hangout at Fan Pier
Fan Pier has one of the best views of the Boston skyline and is a fun place to hang out during the summertime. The Seaport has become very commercialized, so this is one of the only public spaces left to relax among the skyscrapers and luxury apartment complexes.
South Boston (Southie)
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Check out Six West rooftop
Southie is one of the more residential neighborhoods in Boston and is a common place to live for 20-somethings and families. There are some great restaurants on West Broadway here, like Lincoln Tavern and Capo. For a summer drink, I recommend heading to Six West. This rooftop has one of the best views of the Boston skyline and is a fun place for a cocktail and appetizer on a summer evening.
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Hangout at M Street Beach
M Street Beach is a popular place to hang out in Southie and is one of the only beaches within the city limits of Boston. While I recommend venturing north to the Cape Anne (Rockport / Gloucester) area for a beach day or to the South Shore / Cape Cod area, this is a nice place to get your sunset and wine on the beach fix.
The Waterfront
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See the Aquarium / Do a whale watch
This area of downtown Boston is another personal favorite during the summer. This is where you’ll find the New England aquarium, the whale watches, and a few waterfront restaurants. The aquarium is great year-round, but the whale watches that depart from here are one of the best things to do in Boston during the summer. Whale watches are usually quite long, but can be a real treat if you’re lucky enough to spot a humpback!
Pro-tip: Feeling hungry? Check out Tia’s for fun outdoor seating and delicious food overlooking Christopher Columbus Park. Feeling tipsy? Grab a fishbowl at The Landing. Just be warned — they’re sugary and very strong.
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Watch the entertainers in Faneuil Hall
Faneuil Hall is one of the most popular places to hangout in Boston, and is a top thing to do in Boston during the summer. Aside from dozens of shops and restaurants in this area, there’s also Quincy Market and fun street entertainment.
East Boston (Eastie)
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Party on Tall Ship
East Boston, or “Eastie” is one of Boston’s more up-and-coming neighborhoods. It’s residential, with a few stand-out restaurants located near the Maverick T Station. The main attraction that is WELL worth the commute across the harbor here is Tall Ship.
Tall Ship is exactly what is sounds like — it’s a converted tall ship turned bar, docked in Eastie. There are numerous bars on board, along with others, food trucks, games, etc. on the dock. It’s easy to spend a few hours here during the summer months!
Cambridge
Although Cambridge is its own city and is separate from Boston, I would be remiss to not include a few summer suggestions in here.
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Hangout in Harvard Square
Harvard Square is a fun place to explore during the summertime. One of the best places to hangout in this area during a warm day is at Felipe’s Taqueria, which has a fun rooftop bar.
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Take a Duck Boat Tour
This is one of the best things to do in Boston during the summer! A duck boat travels both on land around the city of Boston, and down the Charles River — passing iconic Cambridge landmarks such as MIT, Harvard University, and North Point Park. I HIGHLY recommend looking into this!
Greater Boston
This list could easily be 10,000 words long, but then I’d be repeating information from my ultimate New England bucket list post. Instead, I’m just going to call out a few other regions in Massachusetts outside of Boston for fun summer activities!
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Beaches on the North Shore + Cape Anne
As mentioned above, some of the best beaches in Massachusetts can be found in the Cape Anne area, including Good Harbor, Long Beach, and Halibut Point State Park. Rockport is super charming to walk through, so I recommend grabbing lunch in Bearskin Neck too when you visit!
Rockport Massachusetts
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Beaches on the South Shore + Cape Cod & the Islands
The South Shore includes towns like Scituate, Marshfield, Cohasset, and Plymouth. Plymouth is a fun area to grab drinks and a meal in. The harbor here is nice to walk around during the summertime too. If you continue further south, you’ll eventually cross either the Bourne or Sagamore Bridges onto Cape Cod. There are too many towns here to count, but some of the most “happening” ones during the summer months are Falmouth, Hyannis, Chatham, and Provincetown (P-town). I also highly recommend taking the ferry over to Martha’s Vineyard or Nantucket!
Central + Western Mass
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Go to a drive-in movie
Nothing screams summer like catching a movie at a drive-in! One of the most famous (and only) drive-in movie theaters can be found in Central Mass — the Mendon Twin Drive-In. Arrive early to make sure the show doesn’t sell out!
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Camp in the Berkshires
My number one recommendation for an activity to do in the Berkshires during the summer months leads us back to the sponsor of today’s post — Camp Wylo! Camp Wylo is a (new!) lakeside summer camp for grown-ups, taking place in the beautiful Berkshires region of Massachusetts THIS June 23-25, 2023! Campers can expect a weekend full of childhood camp fun and old school activities. The Camp’s mission is to “host a weekend getaway for adults to unplug, create memories, and enjoy old school fun”. The camp weekend will consist of traditional summer camp activities on the lake, competitions, and leisure time so guests can make meaningful relationships and enjoy life’s simple pleasures in the great outdoors.
Campers can partake in all the preplanned festivities or enjoy the campgrounds at their own pace. There’s no wrong way to enjoy Camp Wylo! Does this sound like something you or a friend would be interested in? Head to Camp Wylo’s website to secure your spot at summer camp today. The bonfires and relay races await.
And that brings us to the end of the best things to do in Boston (and beyond) during the summer! I hope this list inspires you to plan some fun New England activities this upcoming season.
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