Dinner at Jessica’s at Swift House

Located in a beautifully restored historic mansion, Jessica’s at Swift House offers a fine dining experience with a cozy and intimate atmosphere. Indulge in a delicious meal together while enjoying each other’s company in this elegant setting.

Alternative options: The Bobcat Café & Brewery, Two Brothers Tavern

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Wine Tasting at Lincoln Peak Vineyard

Sip on some locally crafted wines at Lincoln Peak Vineyard, located in nearby New Haven. Take a leisurely stroll through the vineyard, sample different wines, and enjoy a relaxing afternoon together.

Alternative options: Boyden Valley Winery, Shelburne Vineyard

Stroll Through Middlebury College Campus

Take a romantic stroll through the picturesque Middlebury College campus and enjoy the stunning architecture and lush greenery. Pack a picnic and relax on the campus lawn for a peaceful afternoon together.

Alternative options: UVM Campus, Champlain College Campus

Live Theatre at Town Hall Theater

Catch a live performance at the historic Town Hall Theater in downtown Middlebury. From plays to musicals, this venue offers a diverse range of entertainment options for a memorable date night.

Alternative options: Vergennes Opera House, Flynn Center for the Performing Arts

Bowling at Green Mountain Bowling

Get competitive with a game of bowling at Green Mountain Bowling. Enjoy some friendly competition, grab a bite to eat at the snack bar, and have a fun and laid-back date night.

Alternative options: Champlain Lanes, Twin City Family Fun Center

Paint Night at Art on Main

Unleash your creative side with a paint night at Art on Main. Enjoy a fun and interactive painting session with your partner, sip on some wine, and create a masterpiece to take home as a memento of your date night.

Alternative options: Sip n’ Paint Studio, The Canvas at Artistree

Ice Cream at Vermont Cookie Love

Indulge your sweet tooth with a visit to Vermont Cookie Love for some delectable ice cream. Treat yourselves to a scoop of your favorite flavors and enjoy a sweet end to your evening.

Alternative options: Goodies Snack Bar, Middlebury Sweets

Hike at Snake Mountain

For the outdoorsy couple, a hike at Snake Mountain offers breathtaking views of the surrounding landscape. Pack a picnic, lace up your hiking boots, and embark on a scenic adventure together.

Alternative options: Mount Philo State Park, Silver Lake Trail

Movie Night at Marquis Theatre

Enjoy a classic date night by catching a movie at the Marquis Theatre. Snuggle up in the cozy theater seats, share a bucket of popcorn, and immerse yourselves in the magic of the big screen.

Alternative options: Majestic 10 Cinemas, Roxy Theater

Couples Massage at Elle Day Spa

Relax and unwind with a luxurious couples massage at Elle Day Spa. Pamper yourselves with a rejuvenating massage treatment and enjoy a soothing and romantic spa experience together.

Alternative options: Bluefern Spa, Green Mountain Oasis

Parents, take the time to prioritize your relationship and reconnect with your partner by planning a date night in Middlebury. Hiring a sitter on Wyndy.com makes it easy to find reliable and trustworthy childcare, so you can enjoy a worry-free evening out. Treat yourselves to a special night together and create lasting memories in this charming town.