Where to Go on a Perfect Date in Boston Right Now
From free performances in the park to discounted oysters, these are the best date ideas in Boston.
Balmy temps are back, and it truly feels like life is beginning anew—which makes it a pretty exciting time to refresh that dating profile. And believe it or not, Boston has plenty of couple-friendly excursions and romantic date ideas, especially as the days hit peak sunniness.
From top-notch bars where you can sip craft cocktails in style to adventurous things to do, we've rounded up 22 stellar ideas that are guaranteed to spice up your date night. So whether you’re dipping a toe back in the matchmaking pool or simply looking to spice things up with your longtime love, here are the best date ideas in Boston right now.
The Commonwealth Shakespeare Company is back, making much ado over Much Ado About Nothing, one of the most charming and romantic Bard plays going. The completely free performances run just about every day, where you can either spread out on your own blanket or lawn chair or rent a chair for $10 on site.
Enough with the remote Peloton dates already. The Minuteman is a well-paced, well-paved trail that takes you through charming parts of Arlington and Somerville and Memorial Drive is once again shut down to four-wheel traffic on Sundays during the summer, so there’s no better time to hop on two wheels with your date.
Here’s a little known fact: In the summer, the main branch of the Boston Public Library hosts free one-hour concerts in its stunning central courtyard—sometimes during lunch, sometimes in the evening. And we’re not just talking classical music. Upbeat jazz, blues, and folk have also appeared on the menu. Make a whole date of it by hitting up the Courtyard Restaurant for full afternoon tea service either before or after the performance.
Cool down together with an all day and night food and drink menu, lounge chairs and cabanas, and a splashy, breezy respite 12 floors up from whatever ails you at street level. If you’re feeling social, rent a cabana and finally go on that double or triple date you’ve been talking about.
Sometimes you just want to embrace the simple pleasures. Exhibit A: a double feature at the drive-in. Mendon Twin Drive-In, located just 50 minutes outside the city in Mendon, shows both first-run flicks and some throwback favorites. Throw open your hatchback, add in a trip to the snack bar and beer garden, and it’s a throwback date for the ages.
Alfresco bivalves with a side of bubbly? Sounds like the ideal day date to us. Island Creek Oyster Farm has reopened its seasonal outdoor bar and hangout spot in Duxbury, which overlooks the water and dishes out beer and wine, canned cocktails, tinned fish, and of course, shucked oysters galore (with the occasional lobster roll pop-up). Plus, leashed dogs are not only welcome but practically de rigeur, so it can be a full family affair.
It was the date of your dreams when you were 14 years old—and you’ll love it just as much today. Grow closer with the help of A4cade’s nostalgic fun: classic ‘80s video games like Galaga and Ms. Pacman and a distinctly grownup cocktail menu. As for that food menu, what’s better on a first date than a couple of grilled cheese sandwiches with a soft-serve chaser?
Tavern of Tales
Looking for a nerdy date night? Tavern of Tales is Boston’s only board game bar, which means you can get off your couch without straying outside your comfort zone. Enjoy unlimited access to the massive board game library plus the opportunity to order from a full beer, wine, and cocktail list. A menu of comfort foods is also available including soup, sandwiches, and desserts like bread pudding and chocolate chip cookies.
The architecture alone is enough to get you and your date excited—never mind the gorgeous courtyard that can give you a floral fix even on a cloudy summer day. While you’re there, swing by the glass-enclosed Café G for a romantic glass of wine and award-winning dessert.
Boston’s love of Fenway Park remains eternal. So head to the park for a tour, and you and your date can wander the grounds, pause on the warning track, and sit atop the Green Monster. Tours run throughout the year, so you can even tour ahead of game time and catch some batting practice before taking your seats for the ultimate Sox lover’s date.
Slurp one-buck shucks
Are they aphrodisiacs? The jury is still out. But the placebo effect has to be worth something, especially when spots around town offer $1 bivalves, including Black Lamb, State Street Provisions, Viale, Lower Mills, Waypoint, Russell House Tavern, and more. Add a martini or two, and you have a date night you’d never know was budget-friendly.
Stopping to smell the roses is one of the oldest—and most effective—moves in the book. Arnold Arboretum is a year-round treat, with 15,000 plants and 4,000 trees that bloom throughout the year, but summer is its obvious time to shine. A leisurely hike up Hemlock Hill followed by a packed picnic under a tree while looking out over the city skyline is the perfect daytime treat.
One thing that came out of this pandemic: a collective deepened love of dumplings and ways to make date night at home a little more exciting. Mei Mei has seized on that reality by offering virtual dumpling-making classes that have remained wildly popular even as we return to adventures outside our homes. So book a class, and settle in for a cozy evening of hand-folding and pan-searing.
Grabbing a drink is a classic early date idea. But if you really want to wow your potential partner, choosing a spot with a romantic ambiance is key. With top-notch cocktails and sweeping views of the city, rooftop bars are a great bet. And we’ve got a list of all the best rooftop bars around town, including newbies like Blue Owl in Central Square and waterfront favorites like Legal Rooftop Bar.
Stargaze at Coit Observatory
Luckily for lovebirds, the BU Coit Observatory opens up its facilities to all us non-scientific types every Wednesday night for its Public Open Night. The viewing starts after sundown and goes for about an hour, leaving you plenty of time for a romantic dinner afterward.
Embark on a walking tour of the city
There are two ways to go: Download any number of the city’s self-guided tours, from the two-and-a-half hour Freedom Trail tour to the fascinating Black Heritage Trail or Women’s Heritage Trail, pop in your matching AirPods, and head out together. Or, harness your inner cartographer and wing it without any recorded guidance. Either way, it’s free, it’s educational, it’s outdoors, and it’s great nerdy fun.
Climb some walls and celebrate with a brew
It’s a lot more fun to work hard and play hard when you have a companion to join you for both. Start with a good old-fashioned forearm workout at Brooklyn Boulders. Once you’ve sufficiently impressed each other and/or humiliated yourselves, head next door to Aeronaut Brewing, where you’ll be asked to do nothing more than sit, drink outside, and be merry.
Every first Friday of the month, all year long, the SoWa arts district welcomes curious passersby into its hub of creativity. Artists fling open their studio doors, showcasing vibrant galleries and keeping them open late so you can pretend to understand what you’re looking at for hours on end. Return on Sunday to shop the dog-friendly SoWa Open Market and SoWa Vintage Market.
Sweat together (for less)
PG-rated heavy breathing on the first date? It’s a good way to find out if you’re fitness compatible. Enter November Project, where early morning, large-scale group workouts take place atop the Harvard Stadium stairs among other outdoor locales, rain or shine. Go forth and flex.
A quaint courtyard in the heart of Union Square, Bow Market has just about everything you need for a fulfilling first date, including outdoor dining, a brewery, and top-quality window shopping. And now that the nights are longer, you’ll see the return of regular live music and other special events.
Stroll through Boston’s prettiest streets
Sometimes simply ambling around one of our favorite Boston neighborhoods is all it takes to win over that special someone. Explore Beacon Hill (at night for extra ambiance) and take in the stunning brownstones for an easy-going but surprisingly charming time. Given all the little shops and restaurants stashed along Charles Street, you’ll find a new conversation starter around every bend.
Coolidge Corner & Brattle Theatre
The iconic Coolidge Corner Theater is back open for business, which means you can once again enjoy first runs and midnight screenings in the flesh. And by showing your support now, you can ensure a future filled with cozy date nights and the best popcorn in town. If you’re a Red Line couple, the Brattle Theatre offers the same throwback allure.