Whether you're a local looking to recharge your routine or a visitor thinking about a quick winter getaway, Chesapeake has you covered with plenty of activities to keep you entertained. From indoor adventures to outdoor explorations, there is no shortage of fun ways to enjoy the season.

Family Fun That's Right Up Your Alley!

Bowling is is always a hit during the colder months. Lucky Strike has two locations - Chesapeake and Western Branch - where you find up to 40 lanes for bowlers of all ages and skill levels. Enjoy street tacos, wings, pizza, and desserts like their monster cookie melt. It's an easy stop for fun with friends and family. 

An indoor ice adventure at Chilled Ponds Ice Sports Complex is a great place to start. Whether you're gliding gracefully or laughing through your first attempts, it is a great way to jump-start your day with fun and exercise. Offering skate rentals and lessons for beginners.

Savor the Flavors at Chesapeake's Tasting Rooms

WineStyles offers a curated selection of wines and craft beers, organized and sorted by style, alongside artisanal cheeses, handcrafted chocolates, and gourmet food. You can explore and learn about different styles of wine through our weekly tastings, educational classes, and winemaker events. Branches Tasting Room offers an impressive selection of wine flights, beer, cider, and even bourbon flights. Pair your drinks with delicious flatbreads or melty sandwiches. If you're in the mood for something stronger, check out Deep Creek Distilling. Open Thursday through Saturday, this artisan distillery offers handcrafted, small-batch spirits made with grain from one of the country's oldest farms. 

An exterior view of the Cinema Cafe
Cinema Cafe

A Little Paint, A Lot of Fun

Feeling inspired to create? Visit GLaZENFYRE or Potts N Paints to paint some pottery. GLaZENFYRE welcomes walk-ins, while Potts N' Paints offers clay pottery, glass, and canvas projects. They even have to-go kits if you prefer creating your masterpiece at home.

Dinner and a Movie

Watch a feature film on the big screen while enjoying a delicious meal at one of Cinema Cafe's two locations - Greenbrier Mall or Edinburgh. Their menu includes pizza, their famous cinnamon swirl cheesecake, and movie-themed cocktails. It's the perfect way to enjoy dinner and a movie without the cleanup!

Explore Scenic Trails

Enjoy nature at its quietest on Chesapeake's beautiful trails. Follow the Battlefield Park path through whispering pines and marshes steeped in Revolutionary War history. Or unwind with a walk around Oak Grove Park's 1.5-mile loop, where wide-open views and calm waters invite you to linger. Each trail offers a beautiful, peaceful way to enjoy the season outdoors.