Trail Running calendar near Pittsfield 2026-2027

Snow or no snow, join the NHTI Lynx on January 10 in Concord for a spirited snowshoe race on scenic college cross country trails with 2 mile, 4 mile and kids events. Proceeds support NHTI Athletics and awards go to top finishers.

The Gurney Lane 5K Snowshoe Race will take place in Queensbury on Saturday 17 January 2026. You can run 5 kilometers.

Join Cock a Doodle Shoe on January 18, 2026 at New Land Trust in Saranac NY for a snowy day of fun and fundraising on snowshoes. Tackle a 5K or 10K or bring kids to the free 1/2 mile scramble.

Join a scenic 6K snowshoe at Natural Stone Bridge and Caves on Jan 24, 2026, with rugged forest trails, caves and mountain views. Part of the DION WMAC series with timing, prizes and limited loaner snowshoes plus a warming bonfire.

Join the Millstone Madness Snowshoe Race on Feb 7 in Websterville VT for a scenic 3 mile loop around old granite quarries on single and double track trails. Snowshoes are required; enjoy friendly competition, prizes, warming fire and raffle..

Join the Frigus Snowshoe Festival at Moreau Lake State Park for fun snowshoe races from a kids mile to a 60K on scenic winter trails. Snowshoes are required and all finishers get medals while top racers earn awards.

Runamuck 50K is a rugged trail ultramarathon around South Pomfret, Vermont, weaving hilly dirt roads and scenic backcountry. Expect changeable weather and a true test of endurance on this challenging 50K course.

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

Run or walk the Ledge Rock Hill Wine Run 5k at Ledge Rock Hill Winery in Lake George on Sunday May 17 2026, a scenic vineyard course welcoming all paces. Enjoy a T shirt, collapsible wine glass and finisher medal while supporting Nik's Wish..

Infinitus is a multiday endurance festival May 21 to 30 in Ripton, Vermont, with distances from 9 miles to 551 miles. Tackle a marathon or join an epic ultrarunning challenge amid scenic Green Mountain forests.

Tackle rugged single track and jeep roads in Keene, NH at the Drummer Hill Trail Races on May 23, 2026. Complete one to four 12.5k laps to choose your distance, enjoy aid stations and earn a drumstick finisher award.

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.

Race the Cirque Series at Cannon Mountain on June 13, 2026, a rugged 6.9 mile climb to the 4,031 foot summit with 3,080 feet of gain. Expect rocky, steep trails and sweeping views on this demanding mountain course.

Run scenic loops around Trapp Family Lodge on June 20 in Stowe Vermont with 25K and 50K options. Wide hard packed trails wind through pastures and hardwood forest with well stocked aid stations for a scenic, challenging race.

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.

Celebrate July 4th at Whiteface Mountain Resort in Wilmington NY with a summit finish atop alpine slopes and serious elevation gain. Race a 10k, a two loop SkyRace, or the Vertical K, then join informal Sunday group runs.

Tackle scenic trail and gravel road courses through the Moosalamoo area of Green Mountain National Forest with sweeping views from Hogback. Choose 5K or 10K and support the Blueberry Hill Outdoor Center while enjoying a friendly community r..

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.