Wine Tasting at Balderdash Cellars

Start your evening with a wine tasting at Balderdash Cellars, a family-owned winery known for its unique and flavorful wines. Sample a variety of reds, whites, and rosés while enjoying the cozy atmosphere of the tasting room. Alternatively, you can visit other local wineries such as Furnace Brook Winery or Les Trois Emme Winery.

Alternative options: Furnace Brook Winery, Les Trois Emme Winery

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Dinner and a Show at Barrington Stage Company

Experience a night of culture with dinner at a local restaurant followed by a show at Barrington Stage Company, a renowned theater known for its innovative productions. Enjoy a delicious meal at Methuselah Bar and Lounge or District Kitchen & Bar before heading to the theater for a memorable performance.

Alternative options: Methuselah Bar and Lounge, District Kitchen & Bar

Painting Class at Berkshire Paint and Sip

Get creative together with a painting class at Berkshire Paint and Sip, where you can enjoy wine and snacks while painting a masterpiece to take home. Unleash your inner artist and create a special keepsake of your date night. Alternatively, you can check out other art studios like Berkshire Paint and Sip or Berkshire Paint and Sip.

Alternative options: Art on No, Paint and Sip Studios

Stroll Through the Berkshire Botanical Garden

Embark on a romantic evening stroll through the beautiful Berkshire Botanical Garden, where you can admire a variety of flowers, plants, and sculptures. Take in the peaceful atmosphere and enjoy each other’s company amidst the lush surroundings. Alternatively, you can visit other botanical gardens such as the Bartholomew’s Cobble or Bidwell House Museum.

Alternative options: Bartholomew’s Cobble, Bidwell House Museum

Hike at Mount Greylock State Reservation

For the adventurous couple, a hike at Mount Greylock State Reservation offers stunning views and a chance to reconnect in nature. Pack a picnic and head to the summit for a breathtaking sunset view. Alternatively, you can explore other trails in the area such as Kennedy Park or Pittsfield State Forest.

Alternative options: Kennedy Park, Pittsfield State Forest

Couples Massage at Simply Serenity Mini Spa

Indulge in a relaxing couples massage at Simply Serenity Mini Spa, where you can unwind and pamper yourselves with a soothing treatment. Let go of stress and tension as you enjoy this intimate and rejuvenating experience together. Alternatively, you can book a massage at Radiance Day Spa or The Spa at Cranwell.

Alternative options: Radiance Day Spa, The Spa at Cranwell

Bowling at Ken’s Bowl

For a fun and lighthearted evening, head to Ken’s Bowl for a game of bowling. Challenge each other to a friendly competition or simply enjoy a casual night out together. Bowling shoes included! Alternatively, you can check out other bowling alleys like Cove Lanes or Imperial Bowl.

Alternative options: Cove Lanes, Imperial Bowl

Comedy Show at the Comedy Garage

Laugh the night away at the Comedy Garage, a local comedy club known for its hilarious stand-up acts and improv performances. Sit back, relax, and enjoy a night of laughter with your partner. Alternatively, you can catch a comedy show at Pittsfield City Improv or the Comedy Connection.

Alternative options: Pittsfield City Improv, Comedy Connection

Dessert Date at Dottie’s Coffee Lounge

Indulge your sweet tooth with a dessert date at Dottie’s Coffee Lounge, where you can enjoy a variety of delicious treats and decadent desserts. Share a slice of cake or a scoop of ice cream as you unwind and enjoy each other’s company. Alternatively, you can check out other dessert spots like Baba Louie’s Bakshack or Chocolate Springs Cafe.

Alternative options: Baba Louie’s Bakshack, Chocolate Springs Cafe

Sunset Picnic at Onota Lake Park

Pack a picnic basket and head to Onota Lake Park for a romantic sunset picnic by the water. Watch the sun dip below the horizon as you enjoy a meal together amidst the peaceful surroundings of the park. Don’t forget to bring a blanket and some wine to toast to your special evening. Alternatively, you can have a picnic at Burbank Park or Lake Mansfield.

Alternative options: Burbank Park, Lake Mansfield