Upcoming Races in Chesapeake

Endurance Grid lists 9 races in Chesapeake, Virginia, from October 2026 to March 2027.

9
Races
2
Sports

Racing in Chesapeake

The Chesapeake race calendar is busiest in January, October, and December. It covers a range of endurance sports — you'll find races in Running and Rucking — so there's usually a race near you. Distances span a wide range across those sports; you'll see 5K, 10K, 1 Mile, 50K, and Marathon, along with other popular distances.

Weather on race day varies by time of year, so it lives where it’s accurate — each race page shows that race’s typical high, low, and rain chance from NOAA climate normals for its venue and date.

Population

251,153

as of 2023

City Elevation

6 ft

Nearest Airport

ORF

Norfolk International Airport

Time Zone

Eastern Time

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Races in Chesapeake, VA

Explore and filter upcoming endurance races in Chesapeake, Virginia on the map below — by sport, distance, price, or month.

9 races in Chesapeake

October 2026 Chesapeake, Virginia Races

2 upcoming races in Chesapeake, Virginia in October.
Oct
17
Sat
Running
JK5K Run/Walk
409 Byron St., Chesapeake, VA
5K
Avg 70° / 53°·6 ft city elevation
Oct–Dec
17–19
Sat–Sat
Rucking
Responders Ruck
Shea Dr, Chesapeake, VA
Avg 88° / 71°·6 ft city elevation

December 2026 Chesapeake, Virginia Races

2 upcoming races in Chesapeake, Virginia in December.
Dec
5
Sat
Running
Chesapeake Rotary Holly Jolly Jog Race and Fun Run presented by the YMCA of South Hampton Roads
173 Mount Pleasant Rd, Chesapeake, VA
1 Mile
Avg 55° / 38°·6 ft city elevation
Dec
6
Sun
Running
Tidewater Strider Dismal Swamp 50K / Marathon /Half Marathon/50K Relay
Rest stop at mile post 4 Dismal Swamp, Chesapeake, VA
Half Marathon · Marathon · 50K
Avg 55° / 38°·6 ft city elevation

January 2027 Chesapeake, Virginia Races

3 upcoming races in Chesapeake, Virginia in January.
Jan
9
Sat
Running
Tidewater Striders 2027 Distance Series #1
1246 Dismal Swamp Canal Trail, Chesapeake 23322, Chesapeake, VA
5K · 10K
Avg 54° / 34°·6 ft city elevation
Jan
16
Sat
Running
Cookie Classic Run
1246 Dismal Swamp Canal Trail, Chesapeake, VA
1 Mile · 5K · 10K
Avg 48° / 32°·6 ft city elevation
Jan
23
Sat
Running
Schock & Shivers 5k and Cold Water Challenge
Timothy Schock Memorial Lake at Oak Grove Park, Chesapeake, VA
5K
Avg 54° / 33°·6 ft city elevation

February 2027 Chesapeake, Virginia Races

1 upcoming race in Chesapeake, Virginia in February.
Feb
27
Sat
Running
Tidewater Striders 2027 Distance Series #3
1246 Dismal Swamp Canal Trail, Chesapeake 23322, Chesapeake, VA
10K
Avg 59° / 37°·6 ft city elevation

March 2027 Chesapeake, Virginia Races

1 upcoming race in Chesapeake, Virginia in March.
Mar
6
Sat
Running
Knights of Columbus Run for Life 5K
424 Albemarle Drive, Chesapeake, VA
5K
Avg 61° / 39°·6 ft city elevation

Races near Chesapeake

Dec
12
Sat
Running
Jingle Jog 5k
3 miles away333 Cedar Road, CHESAPEAKE, VA
1 Mile · 5K
Avg 58° / 38°
Apr
3
Sat
Running
Bunny Hop 5K & 1 Mile Family Fun Run
6 miles awayPortsmouth Pavilion, Portsmouth, VA
1 Mile · 5K
Avg 65° / 45°·11 ft city elevation
Oct
16
Fri
Running
Pink Ribbon Run 5K
6 miles awayNaval Medical Center Portsmouth @ Riverview Fitness Center, Portsmouth, VA
5K
Avg 71° / 53°·11 ft city elevation
May
22
Sat
Road Cycling
VeloCity Youth Tour
7 miles away3017 Kimball Terrace, Norfolk, VA
Avg 77° / 59°·5 ft city elevation
Oct
17
Sat
Running
From Here to Eternity Run Through the Stones 5K Run-Walk
8 miles away238 E Princess Anne Rd, Norfolk, VA
5K
Avg 70° / 53°·5 ft city elevation
Jan
30
Sat
Running
Tidewater Striders 2027 Distance Series #2 at the Historic Fort Monroe
8 miles away100 Stillwell Road, Hampton, VA
8K / 5 Mile · 10 Mile
Avg 55° / 34°·7 ft city elevation
Apr
10
Sat
Running
Don't Struggle In Silence 5k
8 miles away1129 Boissevain Ave, Norfolk, VA
5K
Avg 68° / 47°·5 ft city elevation
Dec
5
Sat
Running
Tacky Sweater 5K
10 miles away2330 Bowdens Ferry Road, Suite 600, Norfolk, VA
5K
Avg 55° / 38°·5 ft city elevation
Oct
31
Sat
Running
Masked Hope 5k Run/Walk
10 miles away310 Edwin Drive, Virginia Beach, VA
2 Mile / 3K · 5K
Avg 66° / 46°·14 ft city elevation
Nov
13
Fri
Running
Wounded Warrior 5K Run
11 miles away1427 Mitscher Avenue (POW/MIA Park), Norfolk, VA
5K
Avg 62° / 45°·5 ft city elevation
Nov
26
Thu
Running
Tidewater Striders Turkey Trot 10K & Mile
12 miles awayMt Trashmore YMCA, Virginia Beach, VA
1 Mile · 10K
Avg 58° / 39°·14 ft city elevation
Jul
4
Sun
Running
43rd Annual Independence Day 5K
12 miles awayMt. Trashmore Family YMCA, Virginia Beach, VA
5K
Avg 87° / 70°·14 ft city elevation

Frequently Asked Questions

How many races are in Chesapeake, Virginia?
Endurance Grid's Race Calendar lists 9 upcoming races in Chesapeake, Virginia, spanning 2 sports.
What kinds of races are held in Chesapeake?
Chesapeake hosts rucking and running races.
Is there a race season in Chesapeake?
Races in Chesapeake run throughout the year rather than in a single fixed season. Of the upcoming races on Endurance Grid's Race Calendar, the most are in January and October.
What race distances can you find in Chesapeake?
Upcoming races in Chesapeake cover distances including 1 Mile, 5K, 10K, Half Marathon, Marathon, and 50K.
What other cities near Chesapeake have races?
Nearby race cities include Norfolk and Virginia Beach.