Kids, this is the story of how I met your mother, and it was all thanks to BOStoday.
Ok, so maybe that’s not exactly how the 2000s sitcom went, but if Ted Mosby had consulted us for date night ideas, we could’ve shaved the show down to two seasons (and saved his kids a lot of time). Regardless, whether you’ve met “the one” or are hoping to impress someone new, we’ve got 25+ local date night ideas that are legen — wait for it — dary.
For the ones who want a night out on the town
- Take in the views at the View Boston observation deck and grab drinks at the Stratus rooftop bar.
- Have a few laughs together at a comedy venue like Improv Asylum or Laugh Boston.
- Pick up eats from the vendors at Time Out Market and visit Fenway Park for a baseball game. Pro tip: Don’t forget to stop by Back Door Donuts before or after the game.
- Stroll the exhibits at the ICA and order drinks at the cafe and wine bar.
- Listen to live music from a local jazz bar like the historic Wally’s Cafe, The Beehive, or Grace by Nia.
If the way to their heart is through their stomach
- Make reservations at a North End restaurant and grab drinks at the Modern underground bar.
- Speaking of the North End — Make your own cannoli tour with a stop at Mike’s, Modern, and Bova’s. Check out how our dessert hot takes compare to yours.
- Try a Korean corn dog and mochi donuts from Kimchipapi Kitchen in Allston.
- Sign up for a cooking class at Cambridge Center for Adult Education.
- Shake things up with a cocktail class and learn how to make classic sips from the team at The Boston Shaker.
- Feast on lobster rolls both ways (Connecticut-style served hot and buttery and a Maine-style chilled with mayo) and other delicious seafood from the Barking Crab on the waterfront.
- Transport yourself to a tropical paradise with a visit to Wusong Road.
- Create your own adventure and see how many delicious bites you can find though the Chinatown neighborhood. Think: Dumplings from Dumpling Cafe or pho from Pho Pasteur.
If you love the great outdoors
- Pack for a Public Garden picnic with bites from Deluca’s Market, or swing by one of the neighborhood farmers markets to fill your basket.
- If you want to explore the waterfront on your own, book an electric boat adventure to tour the Boston Harbor or take a Charles Riverboat Company sightseeing cruise.
- Take a hike. Before you go, consult our guide to 15 hikes with a variety of lengths and difficulty levels.
- Rent BlueBikes and take a ride around Jamaica Pond or the Charles River Esplanade.
- Leave Boston behind and relax on island time with a ferry ride to Spectacle Island to explore the barrier islands.
For the ones who like to play games (just not with your heart)
- Order a gourmet grilled cheese from Roxy’s and walk through the cooler door to the speakeasy-style arcade bar.
- Head to South Boston and let your competitive side show for a round of pickleball or two at PKL.
- Visit Seaport for a round of high-tech mini-golf at Puttshack. Pro tip: Get there early to have a drink and some snacks before your game.
If you’re really hoping that it works out
- Let the endorphins flow with a free workout with Seaport Sweat.
- If you’re in it to win it, register for a road race and train together on one of these scenic paths.
If you want an “old fashioned”-style date
- Make reservations for dinner and walk over to a show at a local theater like the Boch Center or Emerson Colonial Theatre.
- Visit Sullivan’s Castle Island for ice cream and go for a long walk at the M Street beach.
- Sip on cocktails and enjoy conversation at speakeasies like The Wig Shop or Yvonne’s.
- Lace up your roller skates and hit the rink at the Chez Vous Roller Rink.
- Let your artistic side show with a paint class at Tongwood in Brookline. Bonus: An instructor is there to help guide you and no experience is necessary.
If you wanna show off by knowing all the hottest events in town
- Shameless plug: Sign up for our daily newsletter, where we call out our top picks of things to do around town. Your date doesn’t have to know we’re behind it, you can take all the credit.
- Stay up to date on the coolest local events around Boston with our events page (and check out this guide for our tips on navigating the page).
What did we miss? If you know a perfect date spot that’s not on the list, guide us in the right direction using this survey.