Things to Do in Chesapeake (2025)

A nonprofit museum telling the 1775 Battle of Great Bridge and the city’s canal story through interactive exhibits and a boardwalk along the Intracoastal Waterway. Recently spotlighted by WHRO Public Media for its education work, it anchors Chesapeake history with heart.

Locally owned guides lead calm-water paddles on Chesapeake’s Dismal Swamp Canal and Northwest River. Recommended by the city’s tourism editors, trips highlight turtles, herons, and canal lore—no gear or experience required.

Chesapeake’s first craft brewery pours award-winning beers in a garage-inspired taproom with a lawn for families and dogs. Recognized by VEER Magazine and medal-winning at state and national competitions, it’s a relaxed gathering place that supports local causes.

An independent microbrewery in Greenbrier known for creative small-batch lagers and ales, mezzanine seating, and frequent events. Earned praise from regional beer press, including a VEER Magazine nod for its Italian pilsner.

Baseball-themed, family-run brewpub with house-made pizza, salads, and a lineup that skews approachable—plus trivia and music nights. Featured by Visit Chesapeake as a new-wave local brewery with a neighborhood feel.

A small-batch distillery pouring Virginia-made bourbon, rye, moonshine, gin, and vodka in a snug tasting room. Listed by Virginia Spirits, it’s a low-key stop for sampling and bottle shopping on weekend afternoons.

A multigenerational farm bakery and creamery serving scratch pies, sandwiches on house rolls, and ice cream made on-site. Visit Chesapeake highlights the Barnyard for hands-on animal encounters—the kind of everyday farm life that defines the city’s rural roots.

Family-owned U-pick orchard and farm market with seasonal strawberries, peaches, and blackberries, plus a free play area and petting zoo. The city’s tourism calendar regularly features its 2025 picking days.

One of the East Coast’s largest and most active outdoor airsoft fields, run by locals and open most weekends with story-driven events. Visit Chesapeake calls out its varied terrain, on-site pro shop, and spirited community.

A Chesapeake roaster serving morning drinks from a bar inside Big Ugly Brewing. Visit Chesapeake notes partnerships with local bakers and a Friday pop-up from Klassic Doughnuts—an easy pre-adventure caffeine stop.

Independently owned since 2009, this lunch-only spot bakes its own bread and sources locally when possible. Visit Chesapeake and local diners praise its made-from-scratch sandwiches, salads, and soups—simple food done with care.

Locally owned tasting room and bottle shop focused on small producers, with weekly themed tastings and shareable boards. A low-key way to sample beyond the basics and chat with staff who love introducing new regions.

Fourth-generation watermen run this seafood market-restaurant known for Virginia blue crabs, local oysters, and generous steam pots. Featured by Coastal Virginia Magazine’s dining coverage and the city’s visitors bureau, it’s Chesapeake seafood at the source.