Boston’s Coolest and Most Romantic Fall Date Ideas

Cuffing season is just around the corner.

For now at least, the old-school comforts of face-to-face socializing are still on the table. Which begs the question—how does one go about this strange phenomenon called in-person dating? Believe it or not, Boston can still surprise with its couple-friendly excursions. We’ve rounded up 19 stellar ideas for you and your paramour to enjoy all day or all night long this fall, whether you’re dipping a toe back in the matchmaking pool or simply looking to pumpkin spice things up with your longtime love.
 

Russell Orchards
Russell Orchards

It’s cliched, sure, but it’s also why we live (and love) in New England. So grab your flannel and prep your IG stories for some cutesy shots amid the region’s most scenic orchards. And as for those donuts—you can’t beat the made-from-scratch beauts at Russell Orchards, which incorporates its very own apple cider into the batter.

Arnold Arboretum
Arnold Arboretum | quiggyt4/Shutterstock

A visit to the arboretum is a no-cost no-brainer. With 15,000 plants and 4,000 trees blooming throughout the year, you’re hardly ever wanting for bucolic scenery. Hike Hemlock Hill, then spread a blanket under a a shady stunner for some al fresco chill time. And if the actual chill is too much to take, a thermos of hot chocolate should do the trick.

North Road Farm
North Road Farm

Take a beachside horseback ride

Bet you didn’t even know that Crane Beach allows horseback riding in the offseason. North Road Farm offers guided, one- to two-hour beach rides during low tide, allowing you and your sweetie to take your time and soak up those romantic Robin Hood and Maid Marian vibes.

Newport Vineyards
Newport Vineyards

No, we’re not Napa, but New England has its own share of lovely little vineyards—and they’re at their very loveliest in the fall, when the surrounding foliage only enhances the beauty of those headlands and alleyways. If you have it in you to go so far as the Outer Cape, Truro Vineyards are another suburb bet.

AstroStar/Shutterstock

Stargaze at Coit Observatory

Luckily for lovebirds, every Wednesday night the BU Coit Observatory opens up its facilities to all us non-scientific types 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 afterwards. Just don’t forget your masks, which are required for the entire show.

Brooklyn Boulders Somerville
Brooklyn Boulders Somerville

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.

Take in some gratis Shakespeare

Boston Common
Wethinks ‘tis far nobler to experience the Bard in a lawn chair on the Boston Common with a closed container of a little something something. This summer, the Commonwealth Shakespeare Company is back, putting on a complimentary production of The Tempest, a erudite but low-risk date night if there ever was one.

Gerd Hermann/Shutterstock

Pedal along the Minuteman Bikeway

Lexington
Enough with the Peloton dates already. The Minuteman is a well-paced, well-paved trail that guides you through charming parts of Arlington and Somerville. Want to go the extra mile? Rent a tandem bike and hit the road—the front seat selfies alone will be worth the effort.

Tune into the library’s YouTube page… for music

Back Bay
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; jazz, blues, and folk have also appeared on the menu. As expected, the 2020 season was entirely remote. As for Summer 2021, there’s a decent chance that small groups might be allowed in the courtyard at some point but for now, we say roll out a picnic blanket and enjoy from a safe distance.

Mendon Twin Drive-In
Mendon Twin Drive-In

Cruise into a drive-in movie

Mendon
If there’s a silver lining to this pandemic, it’s that we’ve all learned to embrace life’s simple pleasures. Exhibit A: Double features at the drive-in. Mendon Twin Drive-In shows both first-run flicks and some throwback favorites on the weekends after Labor Day. Throw in a snack bar and a beer garden, and it’s a throwback date for the ages.

SoWa Boston
SoWa Boston

450 Harrison Avenue
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.

November Project
November Project

Sweat together (for less)

Various
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. Go forth and flex.

Island Creek Oysters
Island Creek Oysters

Duxbury
Care for a few al fresco bivalves with your 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, wine, canned cocktails, tinned fish, and of course, hand-shucked oysters galore (with the occasional lobster roll pop-up). Plus, leashed dogs are not only welcome but practically de rigeur.

Trillium Brewing Company
Trillium Brewing Company

Various locations
Seasonal al fresco drinking options are not only alive and well, but they’re sticking around well into the colder months. Among the city’s myriad options are the Prairie Fire Beer Garden, Summer in the Square, Trillium on the Greenway, The Beer Garden at W Boston, The Colonnade Pool, Rooftop at Revere, The Anchor, Cisco Brewers Seaport, and the Owl’s Nests on the Esplanade and in Allston.

Embark on a walking tour of the city

Various locations
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.

Museum of Fine Arts, Boston
Museum of Fine Arts, Boston

Fenway
Now open Wednesday through Sunday from 10 am to 5 pm, the Museum of Fine Arts is back in action helping refined Bostonians lose themselves in world famous exhibits. Tickets will cost you $25 per person without a membership, but only $5 on Wednesday from 3 to 4 pm. (Heads up, you’ll have to get your tickets online to facilitate limited-capacity browsing.)

Bow Market
Bow Market

Union Square
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 as soon as the nights start getting crisp, the fire pits will make their comeback.

Stroll through Boston’s prettiest streets

Beacon Hill
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. Judging from all the little shops and restaurants stashed along Charles Street, you’ll find a new conversation-starter around every bend.

Coolidge Corner Theatre
Coolidge Corner Theatre

Coolidge Corner
The iconic Coolidge Corner Theater is finally 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.

Financial District/Waterfront
While you’re out and about downtown, enjoy one of the city’s greatest simple pleasures: the New England Aquarium’s outdoor harbor seal exhibit. If you’d like to get a closer look at aquatic life, the aquarium itself is again open to visitors, but you’ll still have to purchase tickets ahead of time to limit capacity.

Virtual
You love the idea of “trying new things,” but you’re also kind of fine with staying put, especially now that you’ve become so good at it. Thankfully, Cozymeal lets you book online cooking lessons with some of the city’s most celebrated emerging chefs—no fancy new duds required.

Land's Sake Farm
Land's Sake Farm

Weston
On a local farm kick? Land’s Sake in Weston has pick-your-own-flowers, everything from zinnias to snapdragons to sunflowers, and also offers flower arranging classes every Friday. While you’re there, stock up on goodies from the farmstand including honey as well as fruit and other fresh-picked produce.

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Meaghan Agnew is a contributor for Thrillist.