Trail Running Calendar near Waterford 2026-2027

October 2026

Trail Run 5 km 10 km

Trail races at Bradford Preserve on October 3, 2026 feature 5K, 10K and a free kids run on dirt trails with seasonal course markings and a required orange clothing rule per state regulations.

Oct

4

Su

Run the Vineyards - Pindar Fall 8K

Peconic | 26 mi from Waterford

Trail Run 5 km 8 km

Scenic fall 5K and 8K at Pindar Vineyards in Peconic NY with chip timing, water stations, postrace wine for 21 plus, live music and food trucks.

Oct

17

Sa

Ivoryton Pumpkin Chase

Essex | 12 mi from Waterford

Road Race Trail Run 5 km

A 5K road and trail race and a 2 mile walk in Ivoryton to benefit the Ivoryton Library, with a costume prize and t-shirts for early registrants.

Oct

18

Su

Bimblers Bluff 50k

Guilford | 26 mi from Waterford

Trail Run 50 km

An off‑road 50k through southern Connecticut woodlands from Guilford Lakes School, featuring rocky single track and forest roads with a 10 hour cutoff.

Oct

24

Sa

Grills Trail Run

Westerly | 17 mi from Waterford

Trail Run 10 km 10 mi

A fall trail event at Grills Preserve in Westerly with 10 mile and 10 km courses across single-track trails and riverfront sections. Club timing is used, orange clothing is required, and post-race refreshments are provided.

November 2026

Nov

8

Su

Stonington Vineyards Wine Run Turkey Trot 5K

Stonington | 13 mi from Waterford

Trail Run 5 km

A Thanksgiving themed chip timed 5k at Stonington Vineyards on November 8, 2026. The event features vineyard scenery and includes a t shirt, a portable wine glass, a finisher medal that doubles as a wine stopper and a wine pour.

Nov

15

Su

Li'l Rhody Runaround Trail Run

Charlestown | 27 mi from Waterford

Trail Run 4 mi 8 mi

A November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.