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Walking Events Calendar near Chesapeake 2026-2027

Explore the top walking events near Chesapeake for 2026-2027! We've gathered 51 great walks in the area. Check out our detailed list below to find your next local walk.

November 2026
Nov
22
Su

Girls on the Run Hampton Roads 5K

5 km
Nov
26
Th

Tidewater Striders Turkey Trot 10K

10 km
Nov
26
Th

Fast Before the Feast 5K

5 km
Nov
26
Th

Little Neck Turkey Trot and Gobble Wobble

5 km
Nov
26
Th

Charlie Normile's Turkey Trot

Monthly updates for Chesapeake

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Nov
28
Sa

Get Outside 8 Hour

Trail Run 10 km
December 2026
Dec
5
Sa

Tacky Sweater 5K

5 km
Dec
5
Sa

Jingle Bell Run - Newport News

5 km
Dec
6
Su

Dismal Swamp 50K, Marathon, Half Marathon & 50K Relay

13 mi 26 mi
Dec
12
Sa

Santa Claus Shuffle - Portsmouth

Dec
12
Sa

Surf N Santa 5 Miler

5 mi
Dec
19
Sa

Lost in the Woods 5k

January 2027
Jan
1
Fr

Resolution 5K - Virginia Beach

5 km
Jan
9
Sa

Tidewater Striders Distance Series

5 km 10 km 20 km
Jan
16
Sa

Cookie Classic Run

5 km 10 km
Jan
23
Sa

Schock & Shivers 5K

Jan
30
Sa

Tidewater Striders Distance Series - Hampton

5 mi 10 mi 15 mi
February 2027
Feb
27
Sa

Tidewater Striders Distance Series

10 km 20 km 30 km
March 2027
Mar
6
Sa

Knights of Columbus Run for Life 5K

5 km
Mar
27
Sa

Don't Sit on Colon Cancer 5K & 1 Mile Walk

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