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7 romantic date ideas in Greater Boston for fall 2025

Дата публикации: 24-09-2025 20:25:12

Capture all that New England has to offer this fall on these dates with your loved ones.
The post 7 romantic date ideas in Greater Boston for fall 2025 appeared first on Boston.com.


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Fall Foliage Capture all that New England has to offer this fall on these dates with your loved ones. A couple is silhouetted against the fall colors reflected in Leominster State Forest’s Upper Crow Hill Pond. Jessica Rinaldi/Globe Staff

By Kelly Chan

September 24, 2025

2 minutes to read

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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.

Kayak on the Charles RiverA kayaker paddles through Storrow Lagoon along The Esplanade in Boston. – Craig F. Walker/The Boston Globe

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. 

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.

Shucking technique demonstration at Wellfleet OysterFest. – Photo by Lezli RowellFeast 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. 

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 walkMeandering paths originally laid out by Frederick Law Olmsted create a constantly changing vista of fall foliage at the Arboretum. – David Lyon for The Boston Globe

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

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Kelly Chan is a content producer at Boston.com. She designs multimedia content on site and across social media platforms, and experiments with new ways to engage readers.

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