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7 romantic date ideas in Greater Boston for fall 2025
Capture all that New England has to offer this fall on these dates with your loved ones.
As leaves start to fall and temperatures dip, now is the time to get even closer with your loved ones. Here are some date ideas for you and your partner to do this season that capture the New England fall spirit.
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Kayak on the Charles River
Believe it or not, the best time of year to go kayaking is actually autumn. With the color-changing leaves lining the Esplanade, coasting along the Charles River is the perfect way to soak in the fall weather with your date.
Paddle Boston and Community Boating are two popular options for kayak rentals.
Go apple picking
Apple orchards are abundant throughout the region, and some are even consistently ranked as the best by Boston.com readers for both apple picking and apple cider doughnuts. Many popular spots, such as Honey Pot Hill, Cider Hill Farm, and Red Apple Farm, also offer hard cider and live music.
For an even longer stay, you can book a romantic overnight package at several hotels, resorts, and inns with local apple orchards nearby, where some deals even include tea service, dinner, champagne, and more.
Celebrate Oktoberfest at your favorite brewery
It’s time to put on your lederhosen or dirndl because your favorite Boston breweries are ramping up the festivities.
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Get ready for German beers, pretzels, bratwursts, steinholding contests, and more at New England’s Oktoberfest events this season, including celebrations at Sam Adams Brewery from Sept. 26-28 and Harpoon Brewery from Oct. 3-4. Plus, Harvard Square is combining its HONK! Parade and Oktoberfest celebrations on Oct. 12.
Feast at these food festivals
In addition to indulging in apples and lagers galore, you can find harvest parties and fall fests happening all throughout the region. Some are more pumpkin-forward, like the Damariscotta Pumpkinfest & Regatta, while others are simply showcasing New England’s best seafood, like the Wellfleet Oysterfest.
Snuggle up with a spooky film
Your favorite fall movies are being showcased across Greater Boston, with a strong mix of Halloween-themed flicks and sweater-weather cozy films throughout the season.
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See everything from true horrors like “Halloween” (1978) and “The Substance” (2024) to not-actually-scary movies like “Halloweentown” (1998) and “Hocus Pocus” (1993).
Take a scenic hike or walk
Choose from the many hiking trails that Massachusetts has to offer, such as Ashuwillticook Rail Trail in Cheshire, Mount Sugarloaf State Reservation in South Deerfield, and Skyline Trail at Middlesex Fells Reservation in Stoneham. These spots boast some of the best fall foliage views in New England.
If you’re not into hiking, take a stroll through the Arnold Arboretum in Jamaica Plain or along Commonwealth Avenue in Back Bay for the ultimate leaf-peeping experience within Boston.
Tour these Halloween displays
Surprise your date with a bone-chilling experience at New England’s best haunted houses and corn mazes.
And if you’re looking for less fright and more fun, check out the Jack O’Lantern Spectacular in Providence, R.I., with more than 5,000 glowing pumpkins, or Sauchuk’s Corn Maze and Pumpkin Patch in Plympton, which is elaborately designed this year to celebrate the 250th anniversary of the Battles of Lexington and Concord.
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