Trail Running calendar near Chatham 2026-2027

Second annual Kennebec Savings Bank East Bayside Trail Fest in Portland on June 28 2026 offers three trail events plus a post event celebration with music, food trucks and local beer. Proceeds support Portland Trails and the Bicycle Coaliti..

Muddy Princess Maine is a 5K obstacle mud run at Hemond's MX & Offroad Park in Minot, ME on June 28, 2026. The event supports the National Breast Cancer Foundation and includes medals, digital photos, hydration and rinse stations.

A roughly 4.5 mile trail run in Webb Forest near Sunapee, New Hampshire on June 28, 2026, benefiting the Sunapee Middle High School Track and Field program. The course features mountain vistas, single track and varied terrain, with raffle p..

A Fourth of July run/walk in Newport and Derby, VT, on gravel paths and wooded trails with distances from 2 miles to a half marathon; a portion of fees supports NAMI Vermont and ice cream follows the event.

A family oriented 5k on July 4 in Tamworth that begins at historic Ordination Rock, tours village streets and museum trails, includes a bandana, ice cream and a bib raffle, and supports the Tamworth Outing Club.

A backyard ultra around Portland s Back Cove Trail on July 11, 2026. Participants run repeated 4.16 mile loops each hour with two aid locations and on site support until a single runner remains.

A 50K trail ultramarathon made of five 10K singletrack loops through the Spaulding Academy grounds in Northfield NH, with on course aid, drop bags, and a strict eight hour cutoff for the final lap.

A 5.7 mile loop on mostly dirt roads with a 450 ft climb in the first three miles and a gradual descent, held July 11, 2026 at Rumney Memorial School in Middlesex, VT.

An uphill mountain trail race to Loon Mountain North Peak in Lincoln, New Hampshire, roughly 6.03 miles with about 3,066 ft of gain and sections up to a 40 percent grade, featuring over $20,000 in prize money.

A 9-mile, two-lap trail race at Bradbury Mountain State Park in Pownal, ME, featuring hilly, technical single-track, a 3-hour cutoff, and a 160-runner cap as part of the Bradbury Mountain Trail Race Series.

Trail races in Hartford, Vermont, through the Hartford Town Forest and Conservation Area. Courses mix logging roads, packed trails, and single track, with a 5K mostly downhill and a 10K that earns Western NH series points.

An outdoor obstacle race at Sunday River in Newry, Maine, featuring a **5K** course of mud, water, walls and woods, two new obstacles for 2026, a slopeside music event and a separate Mini Mountain kids race.

A July 25, 2026 event in Corinth VT featuring Last Runner Standing and Last Rucker Standing formats with repeated 1 mile loops, an Honor Lap that benefits Northeast Slopes, medals, and a 24th mile fast lap prize.

Trail races in Chatham NH across the Baldfaces with two options, **29KM** (two loops) and **14KM** (single loop); mountain exposure, mandatory gear, aid station for the long course, and a parking area on private property.

A 5K trail race around Barre's historical granite quarries on wooded double and single track trails, with rocky and rooty terrain. Walkers and families are welcome; registration dates and age based fees apply.

A roughly 3.8 mile trail race at Kingman Farm in Madbury, NH on July 26, 2026, featuring rolling nordic style paths and switchback singletrack; proceeds support the Doug Flutie Jr. Foundation for Autism and day of registration is available.

A 5k trail run through Crooked River Forest that starts and finishes at historic Scribner's Mill in Harrison, Maine. Proceeds support Loon Echo Land Trust; registration is via UltraSignup and day-of entries are cash or Venmo only.

A multi-day 75-mile stage race and a point-to-point 50K on the Sunapee Ragged Kearsarge Greenway featuring technical single-track, significant elevation gain, on-course aid stations and transported overnight gear, plus a $35,000 prize purse..

A 12 km trail run on the Oak Hill XC and Trescott Trails in Hanover, NH on August 1, 2026, featuring rolling singletrack, about 1,446 feet of climb and on-course support; pre and day of registration options are available.

The event is cancelled. It had been planned as a 10K ruck obstacle course at Pineland Farms in New Gloucester, Maine, featuring The Crucible with 20+ obstacles and prize rules requiring participants to ruck the full course with a pack.