Virginia · 5K

2026-2027 5K Races in Williamsburg, Virginia

Every upcoming 5K around Williamsburg, with start times, entry fees, finish-time stats from past editions, start-line maps, and the local run clubs to train with.

17 upcoming 5K races found · 9 with finish-time stats

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By the numbers

The Biggest and Longest-Running

The Williamsburg races that stand out on the numbers: the biggest field, and the longest unbroken run of editions.

Largest field730 finishers18th Annual Sleighbell 5K Run/Walkin the 5KLongest-running18th year18th Annual Sleighbell 5K Run/Walkannual tradition
Sun, Oct 11, 20262026 Grove Trotter 5K/10K Bridge Run Williamsburg, VA10K5KFrom $45Details Sat, Oct 17, 2026Dash for CASA 5K Run and Walk Williamsburg, VA5K1 MileFrom $35Details Sat, Oct 17, 2026Haunted 5K, 10K & 13.1M at Williamsburg, VA (42) Williamsburg, VA5K10KHalf MarathonFrom $30Register Sat, Oct 24, 2026The Jamestown Half Marathon, Virginia Company 5K and Discovery Mile Williamsburg, VAHalf Marathon5K1 MileFrom $60Details Sat, Nov 7, 2026Gobbler 5K, 10K, 13.1M, & 26.2M Williamsburg, VA5K10KHalf MarathonMarathonFrom $30Details Sat, Nov 7, 2026Olde Towne's "Stride for Wellness" CARTER'S GROVE 10K Williamsburg, VA10K5K1 MileFrom $40Details Sun, Nov 8, 2026Tunnel to Towers 5K Run & Walk - Williamsburg, VA Williamsburg, VA5KFrom $15Details Sat, Nov 14, 2026The Hare and Tortoise 8K/5K Run Walk, 1 Mile Fun Run Williamsburg, VA1 Mile4.97 Miles5KFrom $45Details Sat, Nov 21, 2026Pie Gobbler 5K, 10K, 13.1M, & 26.2M Williamsburg, VA5K10KHalf MarathonMarathonFrom $30Details Thu, Nov 26, 2026Blue Talon Bistro Turkey Trot Williamsburg, VA5K1 MileFrom $42Details Sat, Dec 5, 2026Holiday 5K, 10K, & 13.1M at Williamsburg, VA (49) Williamsburg, VA5K10KHalf MarathonFrom $30Details Sat, Dec 12, 202618th Annual Sleighbell 5K Run/Walk Williamsburg, VA5K1 MileFrom $35Details Sat, Dec 19, 2026JLHR Jingle Jog 1 Mile Fun Run/Walk & 5k Run/Walk Williamsburg, VA5K1 MileFrom $30Details Sat, Dec 19, 2026Holiday 5K, 10K, & 13.1M at Williamsburg, VA (51) Williamsburg, VA5K10KHalf MarathonFrom $30Register Sat, Feb 13, 202748th Colonial Half Marathon and 5K Williamsburg, VAHalf Marathon5K1.31 Miles5KFrom $40Details Sat, Mar 13, 2027Virginia Fire Chiefs Foundation 5k Williamsburg, VA5K1 MileFrom $30Details Sat, Jun 5, 2027Precarious Beer Hall's Anniversary 5K Williamsburg, VA5KFrom $25Details

How we calculate these stats: RunSesh calculates these figures from the most recent published results of past editions, sourced from RunSignup. We show aggregates only: field size, winning and median times, and the cutoff. We never publish individual finisher tables. Last updated Oct 8, 2026.

Common Questions About Running a 5K in Williamsburg

When are most 5K races held in Williamsburg?

November is the busiest month for 5K races in Williamsburg, with 6 of the 17, followed by October with 4. If you are flexible on the date, that is the quickest way to narrow things down.

Are Williamsburg 5K races beginner-friendly?

Yes, for the most part. Across the 8 5K races in Williamsburg with published results, the typical median finish is around 34:15, which means half of every one of those fields came in slower than that. Recreational runners and walk-runners are the bulk of these fields, not the exception.

Where can I train for a 5K in Williamsburg?

Browse Williamsburg run clubs on RunSesh to find a training group at your pace.

Are there trail 5K races near Williamsburg?

Yes, one race around Williamsburg gets you off the pavement: 1 mixes road and trail.