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Running Calendar near Saint Michaels 2026-2027

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Explore the top running races near Saint Michaels for 2026-2027! We've gathered 40 exciting races in the area. Check out our detailed list below to find your next local race.

Half Marathons Marathons Trail Runs Triathlons
October 2026
Oct
3-4
Sa - Su

Waterman's Triathlon Festival

Triathlon Sprint 750 m 15 mi Sprint 750 m 15 mi 5 km Olympic 1.5 40 km Olympic 1.5 40 10 km
Oct
3
Sa

Friends of the Poor 5K Walk/Run

5 km
Oct
4
Su

Metric Marathon

26 km
Oct
10
Sa

Tom McHugh Arts Scholarship 5K

3 mi
Oct
10
Sa

PRO-Vision Memorial Run

5 km 10 km
Monthly updates for Saint Michaels

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Oct
11
Su

Run the Vineyards - Running Hare 5K

Road Race Trail Run 5 km
Oct
17
Sa

Rev3 Mighty Matapeake

Triathlon Sprint 0.5 12 mi Sprint 0.5 12 3.1 mi Sprint 0.85 12 3.1 mi
Oct
24
Sa

RTB Fair Winds 5K/Fun Run

3 mi
Oct
25
Su

Fore the Fun 5K - Queenstown

5 km
Oct
31
Sa

Historic Drawbridge Running Festival

3 mi 13 mi 26 mi
November 2026
Nov
7
Sa

Downs Park 5 Miler

5 mi
Nov
7
Sa

Jug Bay Run/Walk for Wildlife

Road Race Trail Run 5 km 10 km
Nov
7
Sa

Stride for SPAN Turkey Trot - Millersville

5 km
Nov
8
Su

Bay Bridge Run

Nov
21
Sa

The Tuckahoe 25K

Trail Run 25 km
Nov
24-28
Tu - Sa

YMCA of the Chesapeake Turkey Trot Charity 5K

3 mi
Nov
26
Th

Turkey Trot 5K - Saint Leonard

5 km
Nov
26
Th

North Shore Turkey Trot

3 mi
Nov
26
Th

Camp Letts Turkey Chase

5 km 10 km
Nov
26
Th

Annapolis Turkey Trot

5 km
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