Trail Running calendar near Pittsfield 2025-2026

Enjoy a scenic 5k at Ledge Rock Hill Winery in Lake George with a cross country style course and options to volunteer and run. Finishers get a medal that doubles as a wine stopper, a shirt and a wine pour.

Run Like The Wind 5K in Ellenville offers a scenic course along the Shawangunk Mountains and the newly resurfaced Rail Trail. Finish at Aroma Thyme Bistro for garden drinks and food while supporting local food pantries and youth scholarship..

The Soapstone Mountain Trail Races will take place in Stafford on Sunday 17 May 2026. You can run between 6 and 21 kilometers.

Recharge your trail legs with a small group spring camp in Oliverea, NY, in the Catskills. Tackle technical scrambles and big climbs while getting on trail coaching and mental performance work to sharpen your skills and confidence.

The Drummer Hill Trail Races will take place in Keene on Saturday 23 May 2026. You can run between 13 and 50 kilometers.

Tackle the Mine Hill Half Marathon, a scenic road race that climbs hard in the first half then rewards you with a fast mostly downhill return to Mine Hill Distillery in Roxbury. Finishers get a medal and a lively post race celebration.

IronHike Series Spring 26 takes place June 4 to 7 at Mohawk Mountain, CT, with solo and team endurance options from 15 to 152 miles. This non competitive FlexRelay invites crews to self manage pacing, rest and night trekking.

Run a scenic 5 mile route along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot while supporting the Fitzwilliam and Troy Historical Societies. Food, festivities and a short kids loop make it a great community day.

Take on the slopes at the Plattekill Mountain Race in Roxbury NY on June 7, 2026, where ski runs and forest trails deliver steep climbs, fast descents and sweeping views. Choose the 6.5 mile mountain course or the punchy 5k and race for top..

Join Norbrook Farm Brewery Trail Festival on June 13, 2026 in Colebrook CT for a day of trail runs and mountain bike races on scenic farm trails. Multiple distances, awards and a free beer for those 21 plus create a festive finish.

Take on a scenic 15.7 mile trail run on the Nipmuck Trail in Mansfield CT, following the Fenton River through woods, fields and small bridge crossings. Organized by the Shenipsit Striders, proceeds support local trail stewardship.

Manitou’s Revenge is a 53 mile ultramarathon in the Catskills across rugged, technical trails and massive climbing. Limited aid, long remote stretches and hand over hand sections make it a grueling but rewarding mountain challenge.

The Notchview Ultra will take place in Windsor from Friday 10 July 2026 to Monday 13 July 2026. You can run between 6 and 72 hours.

The Soapstone Assault will take place in Somers on Sunday 26 July 2026. You can run 6 miles.

The Sweltering Summer Ultra will take place in Pittsfield on Saturday 8 August 2026. You can run 8 hours.

The Shenipsit Striders Fatass will take place in Tolland on Saturday 15 August 2026. You can run 5 kilometers.

Climb It For Climate at Belleayre Mountain on August 16, 2026 offers 25K and 8K mountain courses or an early start hike. Join community events, enjoy plant based aid, and support The Catskill Center with an eco conscious approach.

The Jug End Loop Ultra will take place in Great Barrington on Saturday 22 August 2026. You can run 4 miles.

Run the Triple Dam 10K in Perkinsville VT on August 23, 2026 for a scenic road and trail loop with a fun calf deep river crossing. Open to runners and walkers, proceeds support Springfield High School cross country.

Hit the fields at Waters Farm on Sunday, August 23, 2026 for the Old Goat Track Club XC Classic, a fast and friendly 5K cross country through scenic farm trails. A USATF New England Grand Prix stop with race day registration available.