Trail Running calendar near Lincoln 2025-2026

Run a scenic 5 mile Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on Saturday, June 6, 2026. Enjoy family fun, food, and festivities while supporting the Fitzwilliam and Troy historical societies.

Run a scenic 3 mile trail through farm fields and finish among the vineyard rows at Westport Rivers Vineyard and Winery. Celebrate after with wine, music, BBQ and a souvenir glass for a festive postrun party.

Explore rugged singletrack and an old railroad bed on a tough 5 mile loop at the Flat Rock Trail Race in Dunstable MA. Proceeds benefit the Humane Society for Greater Nashua and runners can repeat loops for up to six hours.

Run the scenic 15.7 mile Nipmuck South Trail at Mansfield Hollow State Park, following the Nipmuck Trail along the Fenton River through woods, fields and a climb to a cliff. Proceeds benefit Connecticut trail stewardship groups and the Blue..

Test your trail skills at the Spaulding Woods 50K, a challenging multi lap race on rocky singletrack and scenic footbridges around Northfield, New Hampshire. Well supported and community focused, the event benefits Spaulding Academy & Famil..

The Soapstone Assault is a rugged 5.5 mile trail race in Somers, CT with six climbs and about 1,500 feet of ascent. Limited to 50 runners, it is a tough course for experienced runners and includes a pre race safety briefing and breakfast.

Experience the Stonington Cross Country 5K at Stonington High School, a scenic route from the track through campus streets and wooded trails to a field finish. Family friendly with a kids half mile for ages 10 and under.

Join an 8 hour trail gathering at Crandall's Park and run as many 5K loops as you like. Potluck, raffles, prizes and a Shenipsit Striders 50th anniversary gift for those who complete at least one loop.

Run the Old Goat Track Club XC Classic at Waters Farm in Sutton, a spike friendly 5K cross country loop and USATF New England Grand Prix stop. Perfect for teams and individual racers, with finish line snacks and a nearby after party.

Trail Animals Running Club Fall Classic at Great Brook Farm State Park offers scenic trails and distances from 10K to 50 mile, plus a youth fun run and Mischief Mile. Aid stations and vegan options support runners in this cupless event.

The Mt. A Trail Challenge will take place in York Harbor on Saturday 19 September 2026. You can run 5 kilometers.

Run the newly restored Moosup Valley State Park Trail in Moosup CT with 5K, 10K and a kids fun run on Sunday September 27, 2026. Postrace medallions or tee shirts, food and drink, leashed dogs welcome, and proceeds benefit the Rotary Club o..

Run scenic, rooty trails in Groton Town Forest on October 4 with 9.5 mile and 3.4 mile options through rolling hills and rocks. Limited to 250 runners with refreshments and awards.

Tackle the rugged NipMuck Trail Marathon in Ashford CT, a 26.4 mile trail test through rocks, roots, mud and wooden bridges. Run solo or as a two person relay and expect a challenging, hilly second half that rewards grit.

Hit the trails at the Keene Family YMCA Fall Foliage Trail Races in Keene, NH on Sunday, October 4, 2026, with 5K and 10K options through scenic fall woods. Enjoy chip timing, shirts for early registrants, and support local YMCA programs.

Tackle the Midstate Massive Ultra Trail, a UTMB Index point to point across New England following the historic Midstate Trail. Choose 100 mile, 50 mile or 50k routes through mountains, fields, roads and rivers for a multi state adventure.

Celebrate the 20th Wayland HFC Striders Cross Country Festival on October 11, 2026, a family friendly meet supporting Wayland High School programs. Youth 3K plus open 5K races, trophies and local sponsors make for a fun community day.

Enjoy a scenic 3 mile trail at Sakonnet Vineyard, then celebrate with wine, dinner, music and a souvenir wine glass. BBQ only and kids BBQ options are available for those who prefer to skip the run.

Womp Romp is a trail race at Wompatuck State Park with scenic single track, wider trails, and some paved sections. Choose a 10 mile one loop or a three loop 50K and enjoy friendly aid stations and a community vibe supporting local charities..

Celebrate fall trails at the TARC Stone Cat Trail Festival in Willowdale State Forest in November with distances from a fun Cider Donut Mile to a 100K. Run rugged single track on scenic loops while supporting local conservation groups.