WanderLove: Your Ultimate Road Trip Guide to Chesapeake, Virginia
Experience WanderLove in Chesapeake, Virginia—a profound passion for travel and discovery. Reconnect with nature, family, and scenic drives on a socially distanced road trip packed with outdoor adventures.
Chesapeake delivers family-friendly fun through stand-up paddleboarding, hiking, and restaurants with ample outdoor seating. Easily reachable from western Virginia, Richmond, and Northern Virginia via I-64, or nearby Coastal Virginia spots via US-158 W, it's just a short drive from Virginia Beach Oceanfront, historic Portsmouth, Downtown Norfolk, and North Carolina's Outer Banks.
Perfect for all ages—including pets—plan an extended stay at affordable, pet-friendly hotels or scenic campgrounds for stargazing. In fall, witness stunning foliage along trails and waterways.
Discover six compelling reasons for a WanderLove road trip to Chesapeake, Virginia.
Nature Trails
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Explore Chesapeake's extensive trails and hundreds of acres of lush parks—ideal for biking, hiking, or birdwatching year-round. Shaded paths in summer give way to vibrant fall colors in late October.
Stroll the Chesapeake Arboretum's 48-acre trails with a self-guided tree walk. Enjoy the Dismal Swamp Canal Trail's 16-mile bike loop or 2-mile nature walk. History buffs love the Interpretive Trail at Battlefield Park near the Great Bridge Battlefield & Waterways Museum. Discover all parks and trails Chesapeake offers.
Kayaking Waterways
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Paddle Chesapeake's tidal and non-tidal waterways, including the Dismal Swamp Canal Trail, Northwest River Park, and Elizabeth River Park. Gain serenity, exercise, and family bonding amid stunning natural surroundings.
No kayak? Rent one or join a guided tour with Adventure Kayak & SUP Tours, a family-owned Coastal Virginia outfitter offering custom tours and overnight excursions at prime Chesapeake locations.
South Norfolk Jordan Bridge
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Walk or bike the South Norfolk Jordan Bridge, the region's tallest at 167 feet, spanning the Elizabeth River to Portsmouth. Enjoy panoramic views on the free, pedestrian-safe mile-long path (2 miles round-trip).
Nearby Elizabeth River Park offers a playground, 1/2-mile trail, dog run, 24-hour boat ramp, fishing pier (no license needed), and breathtaking sunsets. Launch kayaks or boats for free.
Breweries & Tap Rooms
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Unwind with craft brews at Chesapeake's breweries. Big Ugly Brewing features 10 bold beers, dog-friendly seating, vintage vehicles, and rotating food trucks—check their Facebook page.
The Garage Brewery, opened in 2019 by local entrepreneur Ulyana Gomez, offers microbrews, spacious indoor/outdoor areas, and snacks in a dog-friendly setting.
Foodie Destinations
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Savor fresh, local flavors from artisanal ice cream to fine dining. Try The Butcher’s Son or Passion The Restaurant; waterfront spots like Big Woody’s Bar & Grill and Lockside Bar & Grill. Pick pumpkins at Mount Pleasant Farms, Greenbrier Farms, Hickory Ridge Farm, or Bergey’s Breadbasket.
Indulge at H.E. Williams Candy Company, Irwin’s Fountain, Wicker’s Crab Pot, or Cutlass Grille. Favorites include Kapers Eatery, The Egg Bistro, McGrath’s Burger Shack, and Racha Thai Cuisine.
Browse the Chesapeake restaurant page for more, including popular chains.
Extend your WanderLove with the Into Chesapeake’s Outdoors itinerary!
