HoodCity Culture β€Ί Chesapeake β€Ί Things To Do
πŸ“… Events & Culture Β· Chesapeake VA 2026

Things To Do
in Chesapeake VA

Jubilee Β· Great Dismal Swamp Β· Black Heritage Trail Β· KayaXpedition Β· Live Music Β· Eagles Nest Β· Northwest River Park
← 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 β€” and Chesapeake is where it lives.

πŸŽͺ Annual Festivals & Events 2026
May 14–17 Β· Chesapeake City Park Β· 43rd Annual Β· 35,000 Attendees Β· $21.25 Pre-Sale
πŸŽͺ CHESAPEAKE JUBILEE 2026 β€” MAY 14–17 Β· 43RD ANNUAL
Chesapeake Jubilee β€” May 14–17, 2026
πŸ“ Chesapeake City Park, Greenbrier Pkwy Β· chesapeakejubilee.org
The city's most beloved annual tradition β€” 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.

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

Tickets: $21.25 pre-sale (unlimited rides) Β· $33 on-site Β· Family 4-Pack $85 Β· Under 3 FREE
April 25 Β· Rotary Club Β· Local Artists Β· Vendors Β· Live Performance Β· Free
🌸 SPRING ARTS FESTIVAL β€” APRIL 25 Β· FREE
Chesapeake Spring Arts Festival
πŸ“ Chesapeake, VA Β· April 25, 2026 Β· Free to attend
Hosted by the Rotary Club of Chesapeake β€” local artists, vendors, and live performance. The community arts kickoff to the outdoor festival season. Free admission.
June 6–7 Β· Northwest River Β· Music + Food Trucks + Kayaks
πŸ›Ά KAYAXPEDITION β€” JUNE 6–7
KayaXpedition 2026
πŸ“ Northwest River, Chesapeake, VA Β· June 6–7, 2026
Annual 2-day kayaking and canoeing event on Chesapeake's Northwest River β€” music, food trucks, kayaks, and canoes for all experience levels. The outdoor summer kickoff.
June 19–22 Β· Battlefield Park Β· Interactive Living History Β· Free
πŸŽ† 250TH INDEPENDENCE CELEBRATION β€” JUNE 19–22 Β· FREE
Chesapeake's 250th American Independence Celebration
πŸ“ Battlefield Park + Chesapeake sites Β· June 19–22, 2026 Β· 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.
September 6 Β· Chesapeake City Park Β· Bagley Stage Β· Free
🎢 VIRGINIA SYMPHONY β€” SEP 6 Β· FREE
Virginia Symphony at Chesapeake City Park
πŸ“ Chesapeake City Park Bagley Stage Β· September 6, 2026 Β· FREE
The Virginia Symphony Orchestra performs live under the stars β€” classic, pop, and jazz. One of the most beloved free cultural events in all of Hampton Roads.
October 12–18 Β· $15+ Prix-Fixe Β· Citywide Β· All Top Restaurants
🍽️ CHESAPEAKE RESTAURANT WEEK β€” OCT 12–18
Chesapeake Restaurant Week 2026
πŸ“ Citywide, Chesapeake, VA Β· October 12–18, 2026 Β· visitchesapeake.com
The city's biggest food event β€” 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.
🌿 Outdoors & Nature
Great Dismal Swamp National Wildlife Refuge
113,000 acres Β· 200+ bird species Β· Black bear Β· Lake Drummond Β· George Washington surveyed it Β· Free trails Β· Black history + Underground Railroad
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Northwest River Park & Campground
763 acres Β· 72 campsites Β· Kayak/canoe/paddleboat rentals $10/hr Β· 18-hole disc golf Β· Equestrian trails Β· (757) 421-7151
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Oak Grove Lake Park β€” TripAdvisor #1 Chesapeake
219 reviews Β· 4.5 stars Β· Kayaking Β· Walking trails Β· "Great area to kayak and be with Mother Nature" Β· FREE
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Great Bridge Lock Park β€” TripAdvisor Top 4
Intracoastal Waterway Β· Battlefield Blvd Β· Boats pass through the historic Great Bridge Lock Β· Free Β· Dramatic waterway views
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Chesapeake Arboretum
48 acres Β· 3.5 miles of trails Β· Antique rose garden Β· Historic Caleb Williamson Farm House Β· FREE daily sunrise–sunset
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✊🏾 History & Black Heritage
Chesapeake African American Heritage Trail
Self-guided trail Β· Underground Railroad Β· 1500s–1900s Lower Norfolk Black history Β· Storyteller Sheila Arnold Β· FREE
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Battlefield Park β€” Virginia Civil War Trails
Battle of Great Bridge 1775 Β· One of the first American Revolution battles in Virginia Β· Free Β· Interactive historical markers
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Dismal Swamp Canal Trail
Surveyed by George Washington 1700s Β· One of the oldest man-made canals in America Β· Biking + hiking Β· Heritage trail Β· FREE
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🎡 Nightlife & Live Music
Eagles Nest Rockin' Country Bar
18,000 sq ft Β· Nashville at the Nest concert series Β· Morgan Wallen, Kelsea Ballerini, Chris Stapleton, Thomas Rhett, Hardy Β· 97.3 The Eagle
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Lockside Bar & Grill β€” Live Music Fri + Sat
200 Battlefield Blvd N, Suite 13 Β· (757) 410-5999 Β· Live music every Friday and Saturday Β· Waterfront Great Bridge canal Β· Craft beers
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Riff House Pub β€” Rock + Metal + Multi-Genre
Chesapeake VA Β· Hampton Roads Reddit community staple Β· "Great people working there and live music often"
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🎯 Family Fun & Indoor Activities
The Slime Lab β€” Yelp's #1 Indoor Activity Chesapeake
Kids hands-on science and sensory play Β· Slime-making experience Β· Kids go wild for it $$
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Glazenfyre β€” TripAdvisor #3 Β· Paint-Your-Own Pottery
4.4 stars Β· 25 reviews Β· Best date night + family activity in Chesapeake $$
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Chesapeake Planetarium
Full-dome planetarium Β· Public shows Β· Free/low cost Β· Most underrated attraction in Hampton Roads
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Hickory Ridge Farm β€” U-Pick Peaches + Petting Zoo
Family farm Β· Petting zoo with goats Β· Barrel train Β· Pony rides Β· U-Pick Peach Orchard every June $–$$
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πŸ“… Full 2026 Chesapeake Events Calendar
Earth Month β€” BIG Tree Tour, Trash Can Painting Contest
πŸ“… Apr 2026 Β· πŸ“ Chesapeake Arboretum + City Parks Β· FREE
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Chesapeake Spring Arts Festival
πŸ“… Apr 25 Β· πŸ“ Chesapeake, VA Β· Rotary Club Β· Local Artists Β· FREE
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πŸŽͺ CHESAPEAKE JUBILEE β€” 43rd Annual Β· 35,000 Attendees
πŸ“… May 14–17 Β· πŸ“ Chesapeake City Park Β· $21.25 pre-sale Β· Fireworks May 17
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πŸ›Ά KayaXpedition β€” Kayaking + Music + Food Trucks
πŸ“… Jun 6–7 Β· πŸ“ Northwest River, Chesapeake Β· $–$$
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250th American Independence Celebration β€” Living History
πŸ“… Jun 19–22 Β· πŸ“ Battlefield Park, Chesapeake Β· FREE
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🎢 Virginia Symphony at Chesapeake City Park β€” Outdoor Concert
πŸ“… Sep 6 Β· πŸ“ Bagley Stage, City Park Β· FREE
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Chesapeake Celebrates Trees β€” Arboretum Events
πŸ“… Sep 26 Β· πŸ“ Chesapeake Arboretum Β· Tree climbing Β· Butterfly exhibit Β· FREE
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🍽️ Chesapeake Restaurant Week β€” $15+ Prix-Fixe
πŸ“… Oct 12–18 Β· πŸ“ Citywide Β· Best food week in Chesapeake Β· visitchesapeake.com
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Live Music at Lockside Bar & Grill
πŸ“… Fri–Sat Weekly Β· πŸ“ 200 Battlefield Blvd N Β· Great Bridge Canal Β· (757) 410-5999 $$
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More Chesapeake Guides
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