Trail Running calendar near Natick 2025-2026

The Drummer Hill Trail Races, held in Keene, New Hampshire, offer runners a choice of distances including 12.5K, 25K, 37.5K, and 50K, based on completing multiple laps of a 12.5K loop. The course features varied terrain, from technical single track to old jeep roads, with significant elevation chang..

The Wine Run at Sakonnet Vineyard is a unique running event scheduled for June 7, 2025, in Little Compton, RI. Participants can enjoy a scenic trail run through the vineyard, culminating in a festive atmosphere with dinner, wine, and live music. The course spans approximately 3 miles and features va..

Run For The Dolls is a 6-hour track ultra running event held at Elliot Field, located at 89 Pearl Hill Road in Fitchburg, Massachusetts. The race challenges participants to run as far as possible within six hours on a track course. The event is capped at 25 runners, with a registration fee of $25 pe..

The Natick Farm Fun Run is a community event held at the Natick Community Organic Farm in Natick, MA. Participants can run, walk, or stroll through a scenic 5K course consisting of three one-mile loops that include road, gravel, grass, and trail surfaces. The route passes by the farmhouse, garden be..

The Nipmuck South Trail Race is a 15.7-mile out-and-back trail run held at Mansfield Hollow State Park in Mansfield, Connecticut. The scenic course follows the Fenton River and features varied terrain including small bridge crossings, a climb to a 50-foot cliff, fields, and woods. Runners navigate t..

The TARC Blue Hills Skyline Trail Run is a challenging 12K race set in the scenic Blue Hills Reservation in Milton, Massachusetts. Participants will tackle approximately 2,300 feet of elevation gain on a rugged course featuring rocky terrain, steep climbs, and technical descents, all while enjoying..

The Edge Hill Trail Race, scheduled for 2025, is a collaborative event with the Franklin Land Trust, celebrating the scenic trails and dirt roads of Ashfield. This race emphasizes a relaxed atmosphere, encouraging participants to enjoy the natural beauty while challenging themselves physically and s..

Last Human Standing in West Greenwich, Rhode Island, is a unique endurance running event held on private property near the Big River Management Area. Participants race on a looped course, each lap requiring completion within 60 minutes to continue. The race begins at 10 AM, with subsequent laps star..

The Flat Rock Trail Race, held in Dunstable, Massachusetts, features a challenging 5-mile loop with nearly 600 feet of elevation gain. The scenic course includes landmarks such as the Arched Bridge Conservation Area, an old railroad bed, a former granite quarry and farm, and climbs to the tops of Bl..

The Summer Solstice Trail Run is an early morning trail running event held at Gay City State Park in Hebron, Connecticut. Scheduled for June 21, 2025, it offers three race distances: 3 miles, 5 miles, and 8 miles. The 8-mile race is part of the 2025 Blue-Blazed Trail Running Series and the USATF-CT..

The Woodland Trail Series, hosted by Tri-Valley Front Runners, is a well-established trail running event held at West Hill Dam in Uxbridge, Massachusetts. Celebrating its 27th year, the series features three races on different dates in June, July, and August, with distances of approximately 5, 4.6,..

The 7-11 Slurpee Day Ultra 60k is a unique self-supported ultramarathon held in Vernon, Connecticut, covering approximately 37.5 miles on mostly road routes. Participants run between multiple 7-11 convenience stores across towns including Vernon, Manchester, East Hartford, West Hartford, Newington,..

The Rails-to-Trails 5K in East Hampton, Connecticut, is a point-to-point race starting at the Connecticut Draft Horse Rescue and finishing at the Old Home Days grounds. The scenic course begins on Chestnut Hill Road, crosses Route 16, and continues along the shaded Air Line Trail for about two miles..

Ocean State Ultra is an endurance running event held at Big River State Management Area in West Greenwich, Rhode Island. The race offers three categories: a 100-mile ultra, a 12-hour, and a 6-hour race, all conducted on a 10-mile loop course featuring 1.5 miles of desert, 1 mile of pavement, and 7.5..

The Soapstone Assault is a challenging approximately 5-mile trail race held at Soapstone Mountain, featuring a unique course that requires participants to climb the mountain six times. This event is designed for those seeking a rigorous hill workout, as runners navigate steep, rocky, and potentially..

The Kingman Farm Trail Race is a welcoming and challenging running event designed for participants of all skill levels. Spanning approximately 3.6 miles, the course features Nordic-style paths and switchback singletrack, making it an exciting experience for runners. This event is organized by acidot..

The Anchor Down Ultra is a premier ultra-marathon event held at Colt State Park in Bristol, Rhode Island. This seaside race features three distinct events: a 6-hour, a 12-hour, and a 24-hour ultra-marathon, catering to various levels of endurance runners. Recognized as one of the "Best Races in Amer..

The Stonington Cross Country 5K is a running event scheduled for August 13, 2025, in Pawcatuck, Connecticut. This event features a 5K race along with a Children's 1/2 Mile, catering to young participants aged 10 and under. The race begins on the track at Stonington High School, followed by a scenic..

The GTA Challenge will take place in Greenfield on Saturday 16 August 2025.

The Tarc Summer Classic is a trail running event held at Noon Hill Reservation in Medfield, Massachusetts, featuring multiple race distances including 10 miles, 50K, and 40 miles. The course is a scenic, mostly forested loop with undulating terrain, roots, rocks, and a notable viewpoint at Noon Hill..