Trail Running calendar near West Bayside 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 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.

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.

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.

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 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.

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.

The 15th Annual 5k Race to the Ledges in Concord, NH on August 8, 2026 features a short road and trail course and includes post-race brunch boxes to take away. Registration includes an adult 5 km entry and a free kids 5 km for ages 6 and un..

A community 5 km run in Derry, New Hampshire on August 8, 2026, with adult and kids categories and online registration closing August 7, 2026.

Trail races of 5k and 10k take place on KCT trails and finish at the headquarters with music, food and a beer tent for a family friendly festival.

A 12 mile single track trail race at Bradbury Mountain in Pownal, ME on August 9, 2026. The course features rugged New England terrain, a 3 hour 36 minute cutoff, and a field limited to 160 runners.

Multi-distance trail ultras in the White Mountain National Forest around Waterville Valley, NH, featuring long climbs, exposed ridgelines, mandatory mountain gear, and live split tracking for the 100, 50, and 20 mile courses.

Wanakee Wilderness 5K on August 15, 2026 is a trail run across 227 acres of hills and woodland valleys in the White Mountains and Lakes Region of New Hampshire. Proceeds support the camp scholarship fund and the day includes a Homecoming BB..

Trail races in Windham, ME on August 22, 2026 with 13 mile, marathon and 50K options on technical single-track loops. Two aid stations, wood carved finisher medals, and a community donation requirement are part of the event.

Trail runs over Vineyard Hill and through Bradley Palmer State Park offering 5K and 10K courses with one Start/Finish aid station, local prizes, and chip timing as part of the North Shore Trail Series.