Seven Fall Date Ideas to Try Out around Boston

Make a DIY movie theater, take a foliage-focused road trip, or even just send food to your new boo across town.

Photo via Getty/Denis Tangney Jr

Another New England fall is upon us, and while we can always count on the changing foliage to keep us outside, we have a few extra reasons to brave the chill this year. Sure, outdoor seating season has been extended, but we need a plan B for date night. Whether you’re meeting up for your first socially distanced date, or you’ve pulled the trigger on getting your nose swabbed (is that second base now?) to make sure you’re both negative, we’ve got date ideas if you’re over Netflix Watch Party.

Take a mini road trip to see some fall foliage 

Maybe your car’s been gathering dust since you started working from home, or the quarantine era has inspired a recent purchase of one. If not, there’s plenty of places to rent a car for the day around the city. Summer may be over, but that just means that leaf-peeping season is upon us. Plan a foliage-filled afternoon using this road trip guide for the best routes around New England. And if you aren’t sure when the best time to go is, use this handy fall foliage prediction map for optimal leaf peep planning.

Playlists are essential to any road trip, but one way you can take the pressure off of playing DJ is by switching song selections using prompts. Your favorite song in 7th grade, the song you listened to non-stop this summer, your guilty pleasure jam, a song from your favorite local artist—you get the idea.

Looking to escape a little longer than just the afternoon? Make it a retro-inspired excursion with a stay at one of these charming motels around New England.

Make your home a DIY movie theater 

Theaters are opening again, and as much as we all want to get back to eating our weight in overpriced popcorn, not everyone is comfortable running back to the big screen just yet. And if there’s one extremely tiny sliver of a silver lining to the “new normal,” it’s that we’ve all gotten a little more creative—and we’re not talking about the half dozen new hobbies you’ve picked up. Upgrade your Netflix and chill situation by making a DIY theater at home with a sheet and small projector. This is perfect if you were part of the exodus to the ’burbs, and a great way to break in your new yard. And though Boston isn’t known for its abundance of green space, you might be able to get away with the set up on your triple-decker for a safer socially distanced movie night at home. Or, if you’re in the “we tested neg” phase of your relationship, you can even bring the operation inside—it’s a good excuse to make a blanket fort.


Yes, surfing. This one might be for the adrenaline junkies. Sure, the West Coast may get the lion’s share of the attention as a surfing destination in the U.S., but you can surf on the East Coast, and the best season isn’t the summer—it’s actually the colder months. Why? Storms in the later months of the year tend to generate bigger and more consistent swells to surf. And besides, you’re a New Englander—you can handle the cold. Don’t have a wetsuit or a board? No worries: There’s more surf shops giving lessons around New England than you’d think. And some are right here in Boston. Here are a few options if you’re ready to hit the waves:

Boston Surf School
Cambridge, MA

Northeast Surfing
Nantasket Beach, Hull, MA

Cinnamon Rainbows
Hampton, NH

Liquid Dreams
Ogunquit, ME

Narragansett Surf & Skate
Narragansett, RI

Make a picnic from the food you get at the farmer’s market 

If you haven’t checked out a farmer’s market this year, there’s still plenty of time—some of the local markets are open into December. Hit one in your neighborhood, or head across town to see somewhere new. Once you’ve got your bag of goodies, plant yourselves at one of these seven social distance-friendly parks around the city. Or, you can always hit Ol’ Reliable, a.k.a. the Esplanade.

A drive-in date

While it seems like every day something new is closing, one operation that has seen a revival during the quarantine era is the traditional drive-in movie theater. Grab dinner and a movie at one of these local “theaters” by picking up your favorite takeout on the way. Another benefit: It’s not weird to bring a pillow and blankets for the show. Hot tip: Snag a spot on the far side of the lot so that when the 5 and under crowd’s bedtime hits, cars aren’t blinding you with their headlights as they leave.

Pick some apples, eat a donut, look at some cranberries 

We’ve got apples, pumpkins, pears—take your pick. And it’s fair game if you’re just in it for the apple cider and fresh cider donuts. Or, if you’ve already crossed those off your fall bucket list, perhaps get lost in a corn maze or take a tour of a cranberry bog. You don’t have to be a cranberry fan to appreciate the unique beauty of a cranberry bog. Not convinced? Take a look at Somerville artist Wilhelm Neusser’s painting, and it’ll surely change your mind.

Send your favorite take-out to each other 

If you don’t feel totally comfortable meeting yet, but you’re having a good time talking, send each other your favorite takeout to eat during your next Netflix Party.