Dinner at Juniper

Start your date night off with a romantic dinner at Juniper. This cozy restaurant offers a seasonal menu with locally-sourced ingredients, creating a unique culinary experience for you and your partner. Enjoy delicious dishes paired with a glass of wine as you unwind and reconnect.

Alternative options: Alta Strada, The Cottage

On-Demand Childcare in Your Neighborhood

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Wine Tasting at The Wine Press

For wine-loving couples, a wine tasting at The Wine Press is the perfect date night activity. Explore a variety of wines from around the world while engaging in lively conversation with your partner. The cozy atmosphere and knowledgeable staff make this a memorable experience.

Alternative options: The Heritage of Sherborn, Urban Grape

Outdoor Movie Night at Elm Bank Reservation

During the summer months, Elm Bank Reservation hosts outdoor movie nights that are perfect for a romantic date night. Pack a picnic basket, grab a blanket, and settle in under the stars as you enjoy a classic film with your loved one.

Alternative options: Medfield State Hospital, Gore Place

Couples Cooking Class at The Paint Bar

If you and your partner enjoy cooking together, consider taking a couples cooking class at The Paint Bar. Learn new culinary skills, bond over a shared experience, and enjoy a delicious meal that you made together. It’s a fun and interactive way to spend your date night.

Alternative options: Sur La Table, Boston Center for Adult Education

Live Theatre at Babson College’s Sorenson Center for the Arts

For a touch of culture and entertainment, catch a live theatre performance at Babson College’s Sorenson Center for the Arts. Enjoy a night of laughter, drama, or music as you and your partner immerse yourselves in the arts.

Alternative options: The Center for Arts in Natick, Weston Drama Workshop

Stargazing at Wellesley College Observatory

For a more low-key and romantic date night activity, consider stargazing at the Wellesley College Observatory. Pack a telescope, some blankets, and a thermos of hot cocoa as you spend the evening marveling at the beauty of the night sky with your partner.

Alternative options: Boston University Coit Observatory, Harvard-Smithsonian Center for Astrophysics

Couples Massage at Winchester Wellness Centre

Indulge in some relaxation and pampering with a couples massage at Winchester Wellness Centre. Unwind together as skilled massage therapists melt away your stress and tension, leaving you both feeling rejuvenated and connected.

Alternative options: Sway Aveda Spa, Boston Bodyworker

Painting Class at Muse Paintbar

Get creative together with a painting class at Muse Paintbar. No painting experience is necessary as a local artist guides you through creating your own masterpiece. Sip on a glass of wine, laugh, and enjoy this fun and interactive date night activity.

Alternative options: The Paint Bar, The Painting Workshop

Sunset Kayaking on the Charles River

For a unique and adventurous date night experience, consider sunset kayaking on the Charles River. Paddle along the scenic river as the sun sets, creating a magical backdrop for you and your partner to enjoy together.

Alternative options: Charles River Canoe & Kayak, Paddle Boston

Dancing at Kings Dining & Entertainment

End your date night on a high note by dancing the night away at Kings Dining & Entertainment. Whether you’re into swing, salsa, or old-school classics, the lively atmosphere and great music make this the perfect spot to let loose and have fun with your partner.

Alternative options: The Blue Ocean Music Hall, The Middle East

As a parent, it can be challenging to find the time and energy to plan a date night. However, it’s essential to prioritize your relationship and make time for each other. By hiring a sitter through Wyndy, you can enjoy a stress-free night out knowing that your kids are in good hands. So, go ahead and plan a special date night in Wellesley Hills, MA with your partner – you deserve it!