Summertime Fun in Chesapeake

Soak up summer in Chesapeake, Virginia, where cool green canopy, winding waterways, and outdoor adventures create the perfect warm-weather escape. Spend your days paddling, biking, hiking, discovering local flavors, and enjoying seasonal farm experiences, then unwind with family-friendly attractions and sweet treats along the way. Whether you're planning a weekend getaway or a longer stay, Chesapeake offers countless ways to enjoy the season.

To help you plan your visit, we've put together a three-day summer itinerary featuring outdoor adventures, local, seasonal flavors, family-friendly fun, and some of Chesapeake's most memorable experiences.

Nothing says summer quite like a fresh, juicy peach. Start your Chesapeake adventure at Mount Pleasant Farms, where you can stroll through the orchard and pick your own peaches straight from the tree. While you're there, spend some time meeting the farm's friendly goats, sheep, and pigs, or stop by to feed the chickens. It's the perfect way to experience Chesapeake's agricultural heritage heritage while enjoying a sweet summer tradition.

After a morning of peach-picking, make your way to Bergey’s Breadbasket for a delicious farm-fresh lunch. Located on a working family farm, the bakery and deli serve sandwiches piled high on freshly baked rolls alongside a variety of sweet treats made right on-site. Be sure to save room for a scoop of their peach ice cream—the perfect summertime indulgence.

Before heading to your hotel, take a relaxing stroll through the Chesapeake Arboretum. This 48-acre natural oasis features winding trails, beautiful gardens, and towering tree canopy that provide plenty of shade on a warm summer day. It's the perfect place to slow down, enjoy nature, and experience another side of Chesapeake before settling in for the evening.

Settle into your Chesapeake hotel and recharge for another day of summer fun. There are a variety of comfortable hotel options throughout the city. Explore our accommodations page to find the perfect place to stay during your Chesapeake getaway.

Wake up refreshed and fuel up for a day of adventure before heading to Indian River Park. Whether you prefer hiking or biking, the park's network of wooded trails offers something for every skill level, including a section of the Virginia Tree Trail. Wind through towering trees, cross charming wooden bridges, and navigate gentle changes in elevation as you explore one of Chesapeake's favorite outdoor recreation spots. It's the perfect way to spend a summer morning immersed in nature. 

After the trails, enjoy a taste of Chesapeake tradition for lunch. Visit Wicker's Crab Pot Seafood for fresh seafood and hometown hospitality. If you're craving classic comfort food, Irwin's Fountain serves up diner favorites and old-fashioned charm that have made it a local institution. Both offer a delicious way to experience Chesapeake before setting out on your next adventure.

Save room for dessert at Look Up Dessert Cafe. Cool off with a refreshing smoothie, sip on bubble tea, or indulge in one of their popular macaron ice cream sandwiches. It's the perfect way to beat the summer heat before continuing your day of exploration.

Spend the afternoon exploring Chesapeake's Greenbrier district. Home to a variety of shopping centers, retailers, restaurants, and entertainment options, Greenbrier offers plenty of ways to relax and recharge after a busy morning outdoors. Browse your favorite stores and discover new favorites. Spend time at Summit Pointe for locally owned eateries and indoor fun at X-Golf.

As evening approaches, settle in for dinner in the Greenbrier area. Enjoy Caribbean-inspired flavors and local hospitality at Cutlass Grille, or savor authentic Thai dishes at Racha Thai Cuisine. Whether you're craving island spices, international flavors, or something in between, Greenbrier's diverse dining scene offers plenty of delicious ways to end another day of summer adventures in Chesapeake.

Wrap up your Chesapeake getaway with a visit to Northwest River Park, a scenic outdoor destination where towering trees, peaceful waterways, and miles of trails invite you to slow down and savor your final day. Pick up lunch to go from a local restaurant and enjoy a relaxing picnic surrounded by nature before setting out to explore the park.

Whether you're looking for adventure or a laid-back afternoon, Northwest River Park offers plenty of ways to enjoy the outdoors. Hike through diverse natural landscapes, challenge family and friends to a round of miniature golf or disc golf, or get out on the water with a canoe, kayak, or stand-up paddleboard. The Northwest River is also a featured stop on Chesapeake's Paddle the Peake, a fun way to experience the city's waterways.

Before heading home, treat yourself to one final Chesapeake dining experience at The Barrel Room. Known for its elevated menu, handcrafted cocktails, and welcoming atmosphere, it's the perfect place to reflect on your seasonal adventure and enjoy a memorable meal. Raise a glass to a great getaway and start planning your next visit to Chesapeake.