Trail Running calendar near Westport 2026-2027

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

The Anchor Down Ultra presents a series of timed ultra-marathons on the coast of Rhode Island. Runners can choose a 6, 12, or 24 hour challenge within Colt State Park.

The Tarc Summer Classic will take place in Medfield on Saturday 8 August 2026. You can run between 10 and 40 miles.

A community eight hour trail event of roughly 5K loops at Crandall's Park in Tolland, CT on August 15, 2026. The day includes a potluck, raffles per loop with prizes, and a 50th anniversary gift for runners who complete at least one loop.

Experience a scenic off-road trail run or walk through the conservation lands of White Barn Farm. This cup-less 5k event supports local sustainable agriculture and community food security in Wrentham.

Experience a scenic trail run through Vineyard Hill Reservation and Bradley Palmer State Park. Choose between 5 km and 10 km distances on a rolling course featuring wide trails and the open landscapes of Shaw Field.

Experience a classic 5k cross country race through the scenic fields of Waters Farm in Sutton. Join the USATF New England Grand Prix season opener on a spike friendly course with both open and masters divisions.

Ocean State Ultra is a loop trail event at Big River Management Area in West Greenwich, Rhode Island offering 100 mile, 12 hour and 6 hour races. The course uses 10 mile loops with trails, short pavement sections, and staffed aid stations.

Traverse the scenic ski slopes and forest trails of Wachusett Mountain in this timed event featuring loops from 7 to 28 miles. Earn a finisher medal within 10 hours and enjoy a post trek party at the mountain base.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

The TARC Fall Classic will take place in Carlisle on Saturday 5 September 2026. You can run between 10 and 50 miles.

Join the Charlie Stavros Memorial Beach Run on September 15, 2026 in Westerly, Rhode Island, a free 3 mile beach run honoring a beloved local runner. Enjoy a scenic low tide out and back along Westerly Town Beach with friends and family.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.

This 5K trail run takes participants through the scenic trails and grasslands of Goddard Park in Warwick. The flat course is open to all ages and abilities. Registration includes a T-shirt and ample parking is available.

Run the Moosup Valley All Trail Race on September 27, 2026. Choose from a 5K, 8K, or 10K on the 100% trail course at Moosup Valley State Park. After the run, enjoy post-race food and a choice of a shirt or medallion.

Trail races and a six hour timed event take place on double track dirt and gravel trails at Assabet River National Wildlife Refuge in Sudbury MA. The race is cupless, aid stations are provided, and pacers are allowed for the six hour event.

Run for Nature in Lowell features a 10K trail run, a 5K run/walk, and a 1-mile kids run at Shedd Park, with educational activities and proceeds supporting local conservation and environmental education.

Survival of the F.I.T.test is a 30 hour trail ultra held in October as part of the F.I.T. Challenge calendar in Cumberland, Rhode Island. Results for past editions are published online after each race.

Experience the beauty of the Bradford Preserve and Woody Hill Management Area in Westerly. This fall trail event features 10K and 5K courses plus a free run for children aged 10 and under.

Experience a scenic trail run or walk through Ryan Park in Rhode Island to support the North Kingstown Firefighters Association with medals for top age group finishers.