Saturday, Oct 01, 2022 9:00a -
Wednesday, Nov 30, 2022 11:00p

Surrounding areas
Boston, MA

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Date Idea, Drinks, Festivals & Fairs, Food, Movies, Music, Nature, Nightlife, Outside, Party, Photoworthy, Seasonal

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A chill is in the air and there’s something spooky lurking in the shadows. There’s no better time to cozy up with your SO and prepare for the season ahead. Maybe you’re the type of couple to drink apple cider and binge watch Harry Potter, or maybe you’re Halloween thrill-seekers (or even ghost-hunters). No matter who you are, fall’s the best time to fall in love.   

1) Enjoy a seasonal drink (or two)

If you’re like us, you prefer getting to know someone over a cold beer (bonus points if its pumpkin flavored!) Try some spooky seasonal drinks at Shore Leave’s new Halloween experience: Scare Leave– it’s bound to be a memorable first date. If you’re both brew-lovers, you might enjoy a Haunted Tour at Aeronaut Cannery, which concludes with a spooky Halloween Party. Enjoy more haunted hops (and candy too) at Bone Up Brewery. If you prefer wine, make sure to check out a guided wine tasting with a sommelier and find out what vino pairs perfectly with your late autumn dishes. If you and your partner would rather indulge in something fancier, take a trip to Lexington and experience Dia de los Muertos Tea at the Inn at Hastings Park

2) Munch on some autumnal snacks 

Treats are better than tricks when you’re out on a date. We’re in the midst of the harvest season, so there’s plenty of opportunities to both get your candy fix and devour some delicious dishes. During the day, enjoy a boo-ze filled Halloween brunch, don your best costume for Cosmica’s Dia de los Muertos fiesta, or explore the city during a costumed Grown-up Trick or Treat! If you want to start making your own meals, why not take a fall foraging workshop or make some delicious fondue for the cold weather ahead? For dessert, make a pie at Powisset Farm

3) Get ready for spooky season 

If you and your date are the curious sort, you might be interested to learn some of the science behind freaky phenomena. Spend a day at the Waterworks Museum to learn the science behind spooky effects (and even check out a magic show!) If you and your SO want a full nightmarish night at the museum, the Boston Children’s Museum will be converted to the Grown-Ups Museum on Oct. 28, where you can face your childhood fears in a terrifying maze and keep an eye out for ghouls and goblins. Or, if you and your date are thrill seekers, you can head to some of the best haunted houses around the city for a spooktacular time. You might find your way through dark catacombs or make your way out of an ancient manor. Regardless of the setting, getting scared is the perfect chance to hold your SO’s hand. Freddie and Daphne, this one’s for you. 

4) Solve a puzzle together

Are you and your date good at problem solving? It's a pretty key element of any relationship. Test your skills at any corn mazes around the city, where you can get lost and found again. It might take hours to make your way out, but at least you’ll be together, right? If you’d rather do something more lowkey (even for a first date!), head to the Ghostly Gardens Scavenger Hunt. Here, you can decipher some clues, sip some hot cider, and find out if you’re compatible detectives. 

5) Work out together 

Working out with someone else gives you double the endorphin boost— so you better stick by your date’s side throughout all the pushups and pull-ups! Plus, you can switch up your routine by trying out some Halloween-themed runs. Boston is home to some of the greatest eerie exercising experiences– from the East 5K Booston to the Great Pumpkin Dash to even the Haunting Halloween Triathlon and Spooky Salsa. Once October ends, keep the momentum going with a fall fitness series, fall yoga, and even the upcoming Turkey Trot. You can get your heart beating– either from the cardio or spending the day with your date. 

6) Bring your pooch along


October is a great month to celebrate puppy love of all kinds. If you and your date are dog lovers just like we are (who isn’t?), then we’ve got just the experiences for you. Take your pup on an adventure to Weston Nurseries’ Halloween Dog Days, attend Polkadogtoberfest, and cap it all off with the Doggone Halloween Parade. They’re all pretty pawesome.

7) Learn about haunted history 

Calling the adventurous couples. This fall, you can investigate some of the creepiest mysteries buried beneath Boston. Start with a tour of King’s Chapel and hear about all the Tales from the Crypt, wander around historic Beacon Hill, and drive to Gloucester to visit the ancient Hammond Castle Museum– perhaps never to return. And if you’re interested in phantoms of the past— but are looking for more casual date ideas— then the Haunted History Slam is a perfect place to start. Too scary? We get it. You can still brush up on history facts this fall with an amazing new history exhibit at the Peabody Essex Museum, a hilarious tour of Boston’s drunken past, and a cool open house at the Colonial Society

8) Watch your favorite fall flick 

The classic movie date is always a good idea. But this fall, you can (pumpkin)-spice things up with some thrilling Halloween movies. After a long day of tricks and treats, you can cuddle up and enjoy a spooky screening. Head to a devilish showing of Haxan at the Scandinavian Cultural Center, grab your SO’s hand during the freaky Night of the Living Dead screening, obsess over the cult-classic Jennifer’s Body, and watch a Halloween showing of the 1978 Halloween. Or, if you’d rather prepare for Thanksgiving early, head to a special Friendsgiving screening with the best of Bill Murray movies. 

9) Party from dusk ‘till dawn

This autumn, you can party from morning to night in places all across Boston. For Halloween, there’s no better place to dress to impress, picking the absolute best costume to show off for your date. Or, go together… perhaps as Morticia and Gomez Addams? Show off your look at the Costume Crawl, party at the 19th Annual Mayhem and Madness Halloween Bash, shake it out at an 80’s Themed Dance Night, sip some spiked cider at the Halloween Pub Crawl, celebrate Dia de Los Muertos, and dance to the Monster Mash at Cheeky Monkey’s Devil’s Carnival. And if you’re not into the Halloween scene, why not check out King Richard’s Faire? It’s the largest and longest-running renaissance fair in all of New England. Or, you could even learn to make some autumnal cocktails together. 

10) Pick pumpkins at a pumpkin patch 

There’s something so romantic about picking pumpkins. In fact, it’s a quintessential New England experience in the fall. Take your date on a day trip to admire the peak-foliage season and find your way to dozens of pumpkin patches. After you’ve picked the perfect pumpkin, you can unwind with a hard cider and live music. If you’d rather not commit to a whole day trip, you and your date can test your creativity at pumpkin carving and share some pumpkin-y beers while you’re at it. 

11) Or, pick some delicious apples

Tell your SO that they’re the apple of your eye. Apple picking is another classic New England experience, and it's the perfect excuse to bring your partner on an autumnal day trip. Munch on spiced donuts, explore the orchards, and sip hard cider at some extraordinary taprooms. It also leads to another perfect date: baking an apple pie together

12) See the fall foliage

The best fall activity is completely free, and it never fails to impress. This fall, watch the leaves change with your date. If you’ve spent a few autumns together, you and your SO might even consider taking a road trip outside of the city for some unique leaf-peeping opportunities.  

13) Enjoy some magical entertainment 

After all the bubble, bubble, toil, and trouble, you and your date will be ready to watch something magical unfold. Cambridge’s Circe’s Circus will awe just about anyone— whether it's a first date or a fiftieth. The enchanting aerials, charmed acrobatics and mystical burlesque will take your breath away. Or, check out The Great Mr. Swindle’s Traveling Peculiarium for a night of surprises. You might even take up magic yourself at the Goblin Market or Brighton Boozar, where you can find spellbound books galore. You can find another bewitching show at Miss Lamplighter's Hallow-Queen Drag Race Special, where the costumes won’t fail to impress. And if you want to know if love’s in your cards, why not get a tarot card reading? Cap off the night of magical entertainment at the Trick or Tease Burlesque show. 

Whether you’re meeting for the first time or you've seen several falls together already, you're in for a treat; Boston has the very best autumnal experiences for you both to try out.


Photo by @bretclancy via Instagram

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10/01/2022 09:00:00 11/30/2022 23:00:00 America/New_York The 13 Best Fall Date Ideas in Boston <p>A chill is in the air and there’s something spooky lurking in the shadows. There’s no better time to cozy up with your SO and prepare for the season ahead. Maybe you’re the type of couple to dri... Boston, Boston, MA false MM/DD/YYYY