Trail Running calendar near New Boston 2026-2027

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 the Sunapee Scramble in New Hampshire on June 7, 2026, a tough 9.2 mile mountain course with 3,250 feet of climbing. As the USATF National Classic Mountain Championship, it also selects the US Classic Up and Down Mountain Running Team.

Explore the inaugural Otter Pond Trail Races in Standish ME, with a scenic 10K, Dawn to Dusk challenge and a kids' fun run around Sebago Lake. Tackle technical single track and marked loops while supporting Bonny Eagle Athletics.

Challenge yourself on the Flat Rock Trail Race in Dunstable MA on June 13 2026 with a scenic 5 mile loop or a 6 hour looped event, featuring rolling climbs and single track trails. All proceeds benefit the Humane Society for Greater Nashua.

Tackle 8.2 miles and 3,010 ft of climbing at the Cirque Series Killington on June 27, 2026, a steep, technical loop that visits three resort peaks and finishes at the K1 Lodge. Expect rocky, grassy trails and a brutal Needle's Eye climb.

Notchview Ultra in Windsor MA, July 10 to 13, 2026 features a scenic 1.9 mile loop with timed options from 6 hours to 100.7 miles. Full aid station, camping and merch plus a lap based charity challenge led by mascot Wally.

Take on a technical 50K in Spaulding Woods New Hampshire, six rugged laps of rocky singletrack, roots, footbridges and about 4,400 feet of climbing. Aid stations and drop bags support runners chasing a 10 hour cutoff.

Run the TARC Blue Hills Skyline 12K on June 21 in Milton, MA, tackling about 2,300 feet of climbing on rocky, technical Skyline trails. Stair climbs and panoramic Boston skyline views make this a memorable trail challenge.

Take on the Summer Hill league at Ardwhallan Outdoor Pursuit Centre in West Baldwin on Sat 18 Jul 2026, a testing 4.5 km trail with 150 m of climb. Pre entry is required and junior entries welcome for a fun, competitive summer race.

Tackle Soapstone Assault, a rugged 5.5 mile trail race up Soapstone Mountain in Somers CT on July 26, 2026, featuring six steep climbs and about 1,500 feet of climbing. Expect rocky, technical terrain and stunning summit views.

Experience a packed 3.6 mile course of Nordic paths, switchback singletrack and varied footing at the Kingman Farm Trail Race. Day of event entry is available and proceeds support the Doug Flutie Jr. Foundation for Autism.

Celebrate the 10th anniversary Ragged 75 around Lake Sunapee, a three stage trail challenge of about 75 miles with 15,500 ft of climbing, or tackle the one day 50k of roughly 33 miles. Camp by the lake, race rugged trails and push your limi..

Experience the Trail Animals Running Club Summer Classic at Medfield's Noon Hill and Shattuck Reservations, a scenic and challenging 10 mile loop of forested singletrack that climbs to a Noon Hill vista. Distances include 10 miles, 40 miles..

Jigger Johnson Ultras offers rugged, technical trail races in New Hampshire's White Mountain National Forest, August 14 to 16, 2026. Choose 20, 50 or 100 mile routes that test navigation, endurance and reward big mountain views.

Run the Triple Dam 10K in Perkinsville VT on a scenic loop of grassy trails, dirt roads and a shallow river crossing. Open to runners and walkers, this fundraiser for Springfield XC finishes by a swimming hole with post race treats.

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.

Join the Black Bear Trail Races in Waterville Valley on Aug 29, 2026. Distances range from a rugged 50K with big climbs to a family friendly 1 mile fun run on beautiful single and double track trails.

Join the Trail Animals Fall Classic at Great Brook Farm for scenic trails and distances from youth fun runs to 50 mile ultras. Community vibe, limited spots, and on course aid make this a favorite, so bring your own hydration and register e..

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

The Vermont 50 is a classic late September mountain bike and ultra run at Mount Ascutney offering 50 mile and 50K options, plus family fun and kids activities on Saturday. Proceeds support Vermont Adaptive Ski and Sports.