Where to Go on a Perfect Date in Boston Right Now
Chill first date spots, sexy speakeasies, and so much more.
Fall is a tricky dating period. Fall foliage and other seasonal activities make it the most wonderful time of the year in New England. But on the other hand, it’s tough to pry us from our homes once temps really start to drop.
But look on the bright side: Cooler weather brings plenty of fun things to do that make for a perfect date night. So whether you’re looking for a cozy cocktail bar or want to get outside for something more adventurous, we’ve got it all on this list of the best date ideas in Boston right now.
There won’t be golden tickets nor edible rivers, but there is a whole lotta chocolate-making going on—and what’s sweeter than that? Taza was once a little-known hipster chocolatier delighting Somerville locals with its open-door policy; today, it’s a national brand that still honors its roots and its early fans. A tour gives you a primer on how to make stone-ground chocolate, from the grinding to the molding, and free samples bring the whole experience home.
Visit a working farm
Food may be the way to a person’s heart, but baby animals come a close second. Our state is awash in open-door farms, from Appleton and Chestnut Hill to Smolak and Russell Orchards (which also has a winery on site). Pet a goat, have some cider, and buy a pie to go for a cozy dinner at home.
Catch a concert at a new(er) venue
Once upon a time, it felt like we were only losing music venues, not gaining them. But then came The Sinclair, Roadrunner, and MGM Music Hall, and suddenly we’re awash in more show options than ever—all the better to determine if you’re musically compatible.
Get uber competitive
OK, so maybe bowling doesn’t feel high-stakes enough. How does an ax sound? With axe-throwing, mini-golf, darts, and ping-pong, our fair burg is now fully immersed in the competitive games scene. Just don’t let your date win; no one should cater to a potential partner’s fragile ego.
First, a primer: Candlepin bowling was developed in Worcester in the 1880s and is a uniquely New England sport. The rules are the same as 10-pin, but the equipment is totally different, requiring palm-sized bowling balls and narrow pins. And Sacco’s Bowl-Haven is the perfect place for couples to try it out, with flatbread pizzas and beers delivered right to your lane.
Take a day trip to Provincetown
P-town is still a delight in late fall—and for many locals, it’s their favorite time of year. Plus, the Provincetown fast ferry runs through mid-December, so in just 90 minutes you can go from downtown Boston to the tip of Cape Cod. Grab lunch at The Canteen, shop the off-season sales on Commercial Street, and spend some time beachcombing and people-watching on one of the in-town beaches. And since your ferry captain is the designated driver, you’re free to indulge and the ferry has drinks for sale on board.
Take a fried clam tour
We Bostonians harbor passionate opinions about where to get the best fried clams, which means you and your potential boo need to be aligned on this front. Head to the North Shore for a daylong taste test; the top three competitors are Woodman’s, JT Farnham’s (open through December), and the Clam Box (also open through December), but dark horses like Essex Seafood could shake up the race.
The Museum of Bad Art is exactly what it says it is—but now, it has a new, more date-friendly home. Dorchester Brewing Company now hangs the fascinatingly horrible art throughout its first floor space; compare notes on your favorite piece of unsightliness while enjoying in-house brews and barbecue from M&M.
Enjoy a speakeasy steak
Is there anything sexier than a delectable ribeye enjoyed behind a red velvet curtain? Bogie's Place, tucked inside jm Curley, is indeed a steakhouse speakeasy and one of the city’s coolest date-night options. The chophouse is just 18 seats strong, doling out classic cocktails, caviar service, a wedge salad, and surprisingly affordable steak cuts, adorned with the likes of bone marrow and foie gras butter.
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?
OK, we’re heading into proposal territory with this one, but it’s pretty high on the romance scale: A private 45-minute tour over all of the city’s most iconic sites, including Fenway Park, the State House, and the USS Constitution. If the ocean beckons, you can instead choose the route that follows the Merrimack River and eventually floats above the North Shore and some of the state’s most beautiful beaches, which are somehow even prettier in the off-season.
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 day. While you’re there, swing by the glass-enclosed Café G for a romantic glass of wine and award-winning dessert.
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.
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.
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.
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 during these shorter days.
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, and be merry.
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.
Every first Friday of the month, 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, warm temps or cold. Go forth and flex.
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.
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 even though it’s getting dark earlier, you’ll still enjoy regular live music and other evening special events.
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 while cozied up to your sweetie noshing the best popcorn in town. If you’re a Red Line couple, the Brattle Theatre offers the same throwback allure.