Things To Do in Chesapeake, VA

Sat 3 Oct 2026 8:00 am

Anchor Scholarship Foundation 5K and FunRun

1246 Dismal Swamp Canal Trail

Sports & Active

Sat 3 Oct 2026 9:00 am

Community Tree Plantings

Bells Mill Park

Sat 3 Oct 2026 10:00 am

Archery 101

Northwest River Park & Campground

Sports & Active

Sun 4 Oct 2026 11:00 am

Waterway Market @ Great Bridge Village

Battlefield Park South

7 more dates through 22 Nov

Sat 3 Oct 2026 8:00 am

Anchor Scholarship Foundation 5K and FunRun

1246 Dismal Swamp Canal Trail

Sports & Active

Sat 3 Oct 2026 9:00 am

Community Tree Plantings

Bells Mill Park

Sat 3 Oct 2026 10:00 am

Archery 101

Northwest River Park & Campground

Sports & Active

Sun 4 Oct 2026 11:00 am

Waterway Market @ Great Bridge Village

Battlefield Park South

7 more dates through 22 Nov

Tue 6 Oct 2026 1:00 pm

Homeschool Adventures: Play Through the Ages

Russell Memorial Library

Kids & Family

Sat 10 Oct 2026 7:30 am

Fall Paddle

Dismal Swamp Canal Trail - 1246 Dismal Swamp Canal Trail

Sports & Active

Sat 10 Oct 2026 10:15 am

5K Angel Run

409 Byron St

Sports & Active

Sat 10 Oct 2026 12:00 pm

Chesapeake Wine Festival

Chesapeake City Park

Festivals & Fairs

Sat 10 Oct 2026 5:30 pm

Sunset Paddle

Great Bridge Lock Park

Sports & Active

Sat 17 Oct 2026 6:30 am

Responders Ruck

Shea Dr

Sports & Active

Sat 17 Oct 2026 9:00 am

JK5K Run/Walk

409 Byron St.

Sports & Active

Sat 17 Oct 2026 1:00 pm

Play Through the Ages: Colonial Games and Toys

Russell Memorial Library

Sat 17 Oct 2026 5:30 pm

Nature's Night Frights

Chesapeake Arboretum

Sports & Active

Thu 22 Oct 2026 9:00 am

Nature Academy: Give a Hoot

Chesapeake Arboretum

Sports & Active

Sat 24 Oct 2026

Invasive Species Removal Days

Chesapeake Arboretum

1 more date through 14 Nov

Sat 24 Oct 2026 8:30 am

Fall Migration Bird Walk

Chesapeake Arboretum

Sports & Active

Sat 24 Oct 2026 10:00 am

Saturday SUNday at Elizabeth River Park

Elizabeth River Park

1 more date through 28 Nov

Thu 29 Oct 2026 6:00 pm

Monster Splash

Western Branch Community Center > Splash Park at Western Branch Community Center

Sat 31 Oct 2026 9:00 am

Community Tree Plantings

Edinburgh Park - 201 Enchantment Trail

Sat 7 Nov 2026 1:00 pm

Horse Appreciation Day

Dismal Swamp Canal Trail - 1246 Dismal Swamp Canal Trail

Sat 7 Nov 2026 5:00 pm

Owl Prowl

Dismal Swamp Canal Trail - 1246 Dismal Swamp Canal Trail

Tue 10 Nov 2026 1:00 pm

Weed Warrior Weekly at the Historical Village at the Dismal Swamp

Historical Village at the Dismal Swamp

2 more dates through 24 Nov

Sat 14 Nov 2026 9:00 am

Fall Colors Walk

Oak Grove Park

Sat 14 Nov 2026 5:00 pm

Campfire tails

Northwest River Park & Campground

Sat 21 Nov 2026 9:00 am

Community Tree Plantings

Sawyer's Mill Park - 2810 Sawyer Arch

Sat 21 Nov 2026 10:00 am

Fall Hiking 101

Northwest River Park & Campground

Sports & Active

Sat 21 Nov 2026 10:00 am

Holiday Craft Show

Chesapeake Conference Center

Classes & Clubs · 1 more date through 22 Nov

Thu 26 Nov 2026 5:00 pm

Deck the Hall

Chesapeake City Hall

2 more dates through 28 Nov

Thu 1 Oct 2026 2:30 pm

Community Engagement Street Team (CEST) at Calvert Square

Calvert SquareNorfolk, 23504 8 mi away

Thu 1 Oct 2026 6:00 pm

WHRO News Local Matters – Military & Veterans Panel Discussion

MacArthur MemorialNorfolk, 23510 8 mi away

Thu 1 Oct 2026 6:00 pm

Business Underground

The SloverNorfolk, 23510 8 mi away

Thu 1 Oct 2026 6:00 pm

Hemp Haven

Virginia Beach areaVirginia Beach, 23456 11 mi away

Fri 2 Oct 2026

Hampton University Men's Tennis vs River City Open

CampusHampton, 23661 18 mi away

Sports & Active

Fri 2 Oct 2026 9:08 am

Hampton University Men's Cross Country vs Richmond Invitational

CampusHampton, 23661 18 mi away

Sports & Active

Fri 2 Oct 2026 10:00 am

Hampton University Women's Cross Country vs Richmond Invitational

CampusHampton, 23661 18 mi away

Sports & Active

Fri 2 Oct 2026 11:00 am

Pups on the Patio with Norfolk Animal Care Center

Starbucks at Wards Corner 7550 Granby St.Norfolk, 23505 8 mi away

Fri 2 Oct 2026 5:00 pm

Breast Run Ever 2026

2044 Landstown Centre WyVirginia Beach, 23456 11 mi away

Sports & Active

Fri 2 Oct 2026 6:00 pm

Norfolk State University Women's Volleyball vs Maryland Eastern Shore

CampusNorfolk, 23502 8 mi away

Sports & Active

Fri 2 Oct 2026 8:00 pm

Lettuce

Elevation 27Virginia Beach, 23451 11 mi away

Sat 3 Oct 2026

Five-Alarm Festival

Syms Middle School, 170 Foxhill RoadHampton, 23661 18 mi away

Festivals & Fairs

Sat 3 Oct 2026 7:00 am

Wealthway Financial Advisors

Virginia Beach areaVirginia Beach, 23456 11 mi away

Sat 3 Oct 2026 8:00 am

Agronomic Lawn Management

Virginia Beach areaVirginia Beach, 23456 11 mi away

Sat 3 Oct 2026 9:00 am

The One of a Kind Financial Show

Virginia Beach areaVirginia Beach, 23456 11 mi away

Sat 3 Oct 2026 9:00 am

Get Your Rear In Gear

300 Butler Farm Rd.Hampton, 23669 18 mi away

Sports & Active

Sat 3 Oct 2026 10:00 am

36th Annual Virginia Children's Festival

Town Point ParkNorfolk, 23510 8 mi away

Festivals & Fairs

Sat 3 Oct 2026 10:00 am

24-Hour Tubs & Showers

Virginia Beach areaVirginia Beach, 23456 11 mi away

Sat 3 Oct 2026 10:30 am

Boombox Rides

Meet at the ERT Trailside Headquarter Building at the corner of Orapax Street and Raleigh Avenue at 10 a.m.Norfolk, 23502 8 mi away

Sports & Active

Sat 3 Oct 2026 11:00 am

Batten University Women's Soccer vs Guilford College

CampusVirginia Beach, 23452 11 mi away

Sports & Active

Sat 3 Oct 2026 11:00 am

The Grimm Sister

Zeiders American Dream TheaterVirginia Beach, 23462 11 mi away

Sat 3 Oct 2026 11:00 am

Equity 1 Inc.

Virginia Beach areaVirginia Beach, 23456 11 mi away

Sat 3 Oct 2026 2:00 pm

Batten University Field Hockey vs Roanoke College

CampusVirginia Beach, 23452 11 mi away

Sports & Active

Sat 3 Oct 2026 4:00 pm

Batten University Men's Soccer vs University of Lynchburg

CampusVirginia Beach, 23452 11 mi away

Sports & Active