Romantic Dinner at Luisa’s Cucina Italiana

Indulge in a delicious Italian meal at Luisa’s Cucina Italiana, known for its cozy atmosphere and authentic cuisine. Share a bottle of wine as you savor dishes like handmade pasta and fresh seafood. For a more intimate experience, reserve a table by the fireplace.
Alternative options: Evergrain Bread Company, Barbara’s on the Bay, The Kitchen at the Imperial

On-Demand Childcare in Your Neighborhood

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Wine Tasting at Cassinelli Winery & Vineyards

Sip on locally made wines at Cassinelli Winery & Vineyards while enjoying the beautiful views of the vineyards. Take a tour of the winery and learn about the winemaking process before settling down for a tasting session. Don’t forget to purchase a bottle to enjoy at home.
Alternative options: Crow Vineyard & Winery, Clovelly Vineyards, Tilmon’s Island Winery

Stroll by the Chester River

Take a leisurely walk by the scenic Chester River with your partner. Enjoy the peaceful surroundings as you chat and reconnect with each other. Watch the sunset over the water for a truly romantic experience.
Alternative options: Wilmer Park, Chestertown Marina, Eastern Neck Island Wildlife Management Area

Live Performance at the Garfield Center for the Arts

Catch a live performance at the Garfield Center for the Arts, a local venue that hosts a variety of shows ranging from plays to musical performances. Enjoy a night of culture and entertainment with your significant other.
Alternative options: The Mainstay, The Prince Theatre, Washington College’s Gibson Center for the Arts

Sunset Cruise on the Chester River Packet Company

Embark on a romantic sunset cruise on the Chester River Packet Company. Enjoy the stunning views of the river and surrounding landscape as you relax on deck with your partner. Don’t forget to bring a cozy blanket to stay warm.
Alternative options: Sultana Education Foundation, Blue Crab Charters, Elsworth Harbor Cruises

Cooking Class at Bad Alfred’s Distilling

Sign up for a cooking class at Bad Alfred’s Distilling and learn how to create a delicious meal together. Bond over food and drinks as you follow along with the chef’s instructions. It’s a fun and interactive way to spend quality time with your loved one.
Alternative options: Crow Vineyard & Winery Cooking Classes, Uncle Charlie’s Bistro, Barbara’s on the Bay Cooking Classes

Couples Massage at Lemon Leaf Spa

Pamper yourselves with a relaxing couples massage at Lemon Leaf Spa. Unwind and de-stress as you enjoy a soothing massage together in a tranquil setting. It’s the perfect way to rejuvenate your mind and body.
Alternative options: The Pearl Modern Spa & Boutique, Bayleaf Therapeutic Massage & Spa, Blue Heron Wellness

Comedy Show at the Mainstay

Laugh the night away at a comedy show at the Mainstay, a local venue known for its intimate setting and talented comedians. Enjoy a night of humor and entertainment with your partner as you share a few laughs together.
Alternative options: Garfield Center for the Arts Comedy Nights, Washington College Comedy Club, The Prince Theatre Comedy Shows

Hike at Eastern Neck National Wildlife Refuge

Explore the great outdoors with a hike at Eastern Neck National Wildlife Refuge. Discover the diverse wildlife and scenic trails as you walk hand in hand with your loved one. Pack a picnic to enjoy a romantic lunch in nature.
Alternative options: Eastern Neck Island Wildlife Management Area, Chesapeake Farms, Chestertown Rail Trail

Painting Class at Create Chestertown

Get creative with a painting class at Create Chestertown. Unleash your artistic side as you follow along with a professional artist to create a beautiful masterpiece. It’s a fun and interactive date night idea that will leave you with a special keepsake.
Alternative options: Clay Studio of Chestertown, Chestertown RiverArts, The Artists’ Gallery

So, why wait? Plan your next date night in Chestertown, MD and enjoy a memorable evening with your partner. Don’t forget to use Wyndy to hire a trusted sitter for your kids, so you can relax and enjoy your night out worry-free.