Things To Do in Chesapeake VA 2026

← Chesapeake

353 square miles. 22+ miles of waterways. The Great Dismal Swamp National Wildlife Refuge. A 43-year community festival. A Black heritage trail spanning 400 years. The 757 doesn't stop — and Chesapeake is where it lives.

🎪 Annual Festivals & Events 2026

May 14–17 · Chesapeake City Park · 43rd Annual · 35,000 Attendees · $21.25 Pre-Sale

🎪 CHESAPEAKE JUBILEE 2026 — MAY 14–17 · 43RD ANNUAL

Chesapeake Jubilee — May 14–17, 2026

📍 Chesapeake City Park, Greenbrier Pkwy · chesapeakejubilee.org

The city's most beloved annual tradition — 43 years running, 35,000+ attendees, 4 days at Chesapeake City Park. Past headliners: Willie Nelson, The Commodores, Chuck Berry, Four Tops, Chris Stapleton, Kansas.

• Kiwanis Shrimp Feast — Thu May 15, 4:30PM–7:30PM
• Main Stage concerts nightly
• Amusements of America — full carnival rides
• Zambelli Fireworks Extravaganza — Sat May 17 ~9PM

Tickets: $21.25 pre-sale (unlimited rides) · $33 on-site · Family 4-Pack $85 · Under 3 FREE

🌐 Get Tickets

April 25 · Rotary Club · Local Artists · Vendors · Live Performance · Free

🌸 SPRING ARTS FESTIVAL — APRIL 25 · FREE

Chesapeake Spring Arts Festival

📍 Chesapeake, VA · April 25, 2026 · Free to attend

Hosted by the Rotary Club of Chesapeake — local artists, vendors, and live performance. The community arts kickoff to the outdoor festival season. Free admission.

🌐 Details

June 6–7 · Northwest River · Music + Food Trucks + Kayaks

🛶 KAYAXPEDITION — JUNE 6–7

KayaXpedition 2026

📍 Northwest River, Chesapeake, VA · June 6–7, 2026

Annual 2-day kayaking and canoeing event on Chesapeake's Northwest River — music, food trucks, kayaks, and canoes for all experience levels. The outdoor summer kickoff.

🌐 Details

June 19–22 · Battlefield Park · Interactive Living History · Free

🎆 250TH INDEPENDENCE CELEBRATION — JUNE 19–22 · FREE

Chesapeake's 250th American Independence Celebration

📍 Battlefield Park + Chesapeake sites · June 19–22, 2026 · FREE

Interactive living history, colonial trade demonstrations, and hands-on educational activities at the historic Great Bridge Civil War battlefield sites. Chesapeake's 250th anniversary event.

🌐 Details

September 6 · Chesapeake City Park · Bagley Stage · Free

🎶 VIRGINIA SYMPHONY — SEP 6 · FREE

Virginia Symphony at Chesapeake City Park

📍 Chesapeake City Park Bagley Stage · September 6, 2026 · FREE

The Virginia Symphony Orchestra performs live under the stars — classic, pop, and jazz. One of the most beloved free cultural events in all of Hampton Roads.

🌐 Details

October 12–18 · $15+ Prix-Fixe · Citywide · All Top Restaurants

🍽️ CHESAPEAKE RESTAURANT WEEK — OCT 12–18

Chesapeake Restaurant Week 2026

📍 Citywide, Chesapeake, VA · October 12–18, 2026 · visitchesapeake.com

The city's biggest food event — prix-fixe menus starting at $15 across the best restaurants in Chesapeake, with special wine and beer pairings. Every top restaurant in the city participates. The best week to eat in Chesapeake all year.

🌐 Details

🌿 Outdoors & Nature

Great Dismal Swamp National Wildlife Refuge

113,000 acres · 200+ bird species · Black bear · Lake Drummond · George Washington surveyed it · Free trails · Black history + Underground Railroad

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Northwest River Park & Campground

763 acres · 72 campsites · Kayak/canoe/paddleboat rentals $10/hr · 18-hole disc golf · Equestrian trails · (757) 421-7151

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Oak Grove Lake Park — TripAdvisor #1 Chesapeake

219 reviews · 4.5 stars · Kayaking · Walking trails · "Great area to kayak and be with Mother Nature" · FREE

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Great Bridge Lock Park — TripAdvisor Top 4