Trail Running calendar near Sunapee 2026-2027

A 50 mile point to point ultramarathon from Manchester, NH to Mount Monadnock with about 6000+ feet of gain over road, dirt road and trail. GPX only navigation, limited to 125 runners, with aid stations about every 10 miles.

Wason Pond Wrangler is a family friendly obstacle course trail race around Wason Pond in Chester, New Hampshire with a *5K* route and more than ten obstacles. The event raises funds for local nonprofits and welcomes individuals and teams.

The Trav's Trail Run will take place in Newburyport on Sunday 17 May 2026. You can run 3 miles.

Experience a scenic trail run through the Phillips Exeter Academy woods. This event features a 5K race for all ages and specific fun runs for children 12 and under with on site activities and childcare.

A series of rugged trail races in Ripton, Vermont from May 21 to 31, 2026 offering distances from 9 miles to 250 miles plus multi‑marathon and ultra challenges. Camping is available for a one time fee; the event is cup free and no refunds.

Trail races in Keene, NH on a revised, technical course where runners choose how many 12.5k laps to run. Natural single track and jeep roads, cupless aid stations, parking at Fuller Elementary School, and drumstick awards.

Run or walk through the scenic Wildcat State Forest Trail in Boxford. This bird friendly event features separate courses for runners and walkers starting at the Danvers YMCA Camp overlooking Stiles Pond.

Test your endurance at the Ascutney Mountain Run in Vermont. This 3.7 mile uphill race climbs 2,300 vertical feet along a paved auto road to a scenic mountain summit finish.

A scenic 2.5 mile off-road run or walk around Horn Pond paired with a festival at Ice House Park featuring food trucks, a DJ, raffles, kids activities, and over 25 local mental health and substance use providers.

A 23 km lollipop trail race in the White Mountain National Forest around Mt Chocorua with roughly 4,500 feet of elevation gain, technical rocky trails, mandatory mountain gear, and a 250-runner field.

A trail event on Wrights Mountain in Bradford, Vermont on June 6, 2026, with a 5K summit climb and a 1.5 mile fun run for ages 13 and under. Proceeds support the Friends of Wrights Mountain Fund.

Sunapee Scramble on June 7, 2026 is a 9.2 mile up and down mountain race with 3,250 feet of vertical, serving as the 2026 USATF National Classic Mountain Championship and the selection race for the US Classic Up and Down team.

Experience a 6.9 mile mountain race at Cannon Mountain featuring 3,080 feet of elevation gain. Run through technical ski trails and rocky ridges to reach a 4,031 foot summit with views of Franconia Notch State Park.

A five mile fun run along the Cheshire Rail Trail from the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.

Experience a scenic New England trail event in Dunstable with a 5 mile loop or a 6 hour timed challenge. Support the Humane Society while running through historic quarries and former ski hills.

Explore the hill towns of western Massachusetts on a mix of trails and dirt roads. Choose from a 50k, 30k, or 10k distance, with all proceeds supporting the Franklin Land Trust's conservation efforts at the scenic Edge Hill Conservation Are..

A trail race in Newport, New Hampshire on June 13, 2026 offering 6 and 3 mile routes through rocky, rooty, hilly forest trails. Proceeds support Newport Recreation and town forest trails and awards are pure New Hampshire maple syrup.

Experience a unique mountain race alongside the historic Cog Railway to the summit of Mount Washington. Choose between a steep 2.75 mile climb or a technical 5.5 mile round trip through the rugged Presidential Range.

Experience a 5k obstacle mud run designed for unity and women empowerment at Kimball Farm in Haverhill. Join a supportive community for a day of teamwork and mud while supporting the National Breast Cancer Foundation.

Experience a mountain run at Killington Resort featuring 3,010 feet of vertical gain over 8.2 miles. Runners summit three peaks and tackle a steep 45 percent grade climb before finishing at the K1 base area.