Home / Hampton Roads / Winter 2026-27 / Trail races
Winter trail races near Hampton Roads (2026-27)
Updated
5 trail races are on the calendar near Hampton Roads in winter 2026-27, starting with Tacky Sweater 5K on Saturday, December 5 in Norfolk. That covers December to February. 4 of them publish an upcoming price increase, so signing up early saves money.
All winter races5K races (21)10K races (10)Half marathons (10)Trail races (5)
By date
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from $40Goes up Dec 4
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Sat Dec 5 · 3:00 PM · Williamsburg · Newport News, Hampton & Williamsburg
Half marathonTrail
from $35Sign up ↗ -
Sat Dec 12 · 9:00 AM · Williamsburg · Newport News, Hampton & Williamsburg
1 mile5KTrail
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Sat Jan 16 · 9:00 AM · Chesapeake · Norfolk, Chesapeake & Suffolk
1 mile5K10KTrail
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Sat Feb 27 · 8:30 AM · Chesapeake · Norfolk, Chesapeake & Suffolk
10K20K30KTrail
Other seasons near Hampton Roads
Quick answers
How many trail races are near Hampton Roads in winter 2026-27?
5 trail races are listed near Hampton Roads in winter 2026-27. The first is Tacky Sweater 5K on Saturday, December 5 in Norfolk, and the last is Tidewater Striders 2027 Distance Series #3 on February 27.
What is the cheapest trail race near Hampton Roads in winter 2026-27?
Cookie Classic Run on January 16 has the lowest listed entry fee: $5. Prices are before the registration platform's processing fee.
When does the next early-bird price end for trail races near Hampton Roads?
Cookie Classic Run: the 5K goes from $45 to $48 after November 25. 3 more of these trail races publish a later price increase.
Are there half marathons or marathons near Hampton Roads in winter 2026-27?
Yes: 1 half marathon and 0 marathons. The first is Run the River Ultra on December 5.