Maine fun runs
34 seasonal, themed and one-of-a-kind fun runs in Maine.
Holiday and seasonal: 12 · Novelty course: 8 · Food and drink: 6 · Quirky format: 3 · Iconic tradition: 2 · Mud and obstacle: 2 · Animals: 1
- Novelty course Sugarloaf Uphill Climb Runners go straight up Sugarloaf's ski trails, about 2,500 vertical feet in roughly three miles, to the 4,237-foot summit (sometimes in snow), then hike down for lunch and a free beer.
- Holiday and seasonal Tour de Gourd 5K & Walk (Damariscotta Pumpkinfest) The route runs down a closed Main Street past Pumpkinfest's carved giant pumpkins and finishes downhill at the prize-winning giant pumpkin on Elm Street Plaza.
- Holiday and seasonal Bath Area Family YMCA Haunted Hustle 5K & Kids Fun Run A costumed Halloween 5K followed by a family harvest festival with bounce houses, pumpkin decorating and an open swim at the Y.
- Holiday and seasonal Monsters Run The River Billed as southern Maine's spookiest race, with a separate Canine 5K so costumed runners can bring costumed dogs along the Presumpscot River.
- Novelty course ASC Long Sands Beach Run A two-lap 5K run entirely on the hard-packed sand of Long Sands Beach, timed for low tide on Halloween morning.
- Holiday and seasonal Trick or Trail: A Costumed 5K Trail Run at the Wells Reserve at Laudholm A costumed trail 5K run on Halloween itself through the 2,200-acre Wells Reserve's meadows, woods and wetlands.
- Holiday and seasonal Kennebunk Outfitters Turkey Trot Listed as Maine's largest Thanksgiving trot by finishers (560 in 2025), on a course along Kennebunk's oceanfront Beach Avenue.
- Holiday and seasonal Portland Thanksgiving Day 4-Miler & Kids K A 45-year Thanksgiving tradition that started with $2 entries after a high-school football game and now loops twice through Portland's Old Port, drawing nearly 1,000 runners.
- Holiday and seasonal Catch That Turkey 5K A YMCA staffer in a turkey costume gets a head start, and anyone who passes the turkey goes into a raffle for a Bartlett Bakery dessert.
- Iconic tradition Millinocket Marathon & Half A free marathon and half in a north-woods mill town, created to bring winter visitors to Millinocket. Its motto: 'Don't run Millinocket for what you get, run Millinocket for what you give.'
- Holiday and seasonal Santa Shuffle 5K Walk/Run for the Children A lakes-region holiday 5K where Santa hats and holiday sweaters are the dress code, with cocoa, cookies and Santa at the finish and an after-party at the Queens Head Pub.
- Holiday and seasonal Ugly Sweater 5K & Merry Mile An early-December ugly-sweater 5K with a shorter Merry Mile, so families can run it together.
- Holiday and seasonal Weirs Motors Seaside Santa Dash Register by Nov. 1 and you get a free Santa (or elf) suit, then run the beaches and roads of the Kennebunks and finish with two Shipyard beers at Federal Jack's brewpub.
- Quirky format Indoor Insanity 5K A January 5K run as dozens of laps on an indoor track at Colby College, with heats by pace and a 'chaos' heat for anyone who wants it.
- Novelty course Portland Sea Dogs Mother's Day 5K The team mascot Slugger and his mom lead the field, which runs behind the bleachers into center field and finishes in front of the third-base dugout at Hadlock Field.
- Quirky format Down East Sunrise Trail Relay Teams of four to eight run 102.7 miles through the night on a rail trail and back-woods ATV track, finishing at the seawall in Eastport, the easternmost city in the U.S.
- Quirky format Almost Half Way to St. Patrick's Day 5K A September 'St. Patrick's' race that celebrates being almost halfway to the holiday, run around Portland's Back Cove.
- Novelty course Bar Harbor Bank & Trust Half Marathon & Fall 5K About 9 miles of the half marathon use Acadia's Rockefeller carriage roads, which are closed to cars and cross stone bridges.
- Food and drink Boots and Brews 5K A downtown Freeport 5K honoring the town's boot-making history (L.L. Bean among them), with two beers from local breweries and a cookout at the finish.
- Novelty course Bridge the Gap Road Race Runners cross the Penobscot Narrows Bridge, home to a bridge-top observatory, on 3- and 10-mile routes from Fort Knox to Bucksport.
- Novelty course Chebeague Island 4th of July Fun Run & Road Race A 46-year Fourth of July tradition on a Casco Bay island reachable only by ferry.
- Holiday and seasonal Irish Road Rover 5K A 30-year St. Patrick's run hosted by Rí Rá Irish pub on Portland's waterfront, rooted in an early-morning St. Patrick's Day run some friends held in Syracuse.
- Food and drink Machias Blueberry 5-Mile Run/Walk & 1-Mile Fun Run The morning race of the Machias Wild Blueberry Festival, which crosses the dike on the Sunrise Trail and finishes before the festival's pie-eating contest lottery opens.
- Food and drink Maine Lobster Festival 10K/5K Road Race Timed road races that open the Maine Lobster Festival, with packet pickup on the festival grounds.
- Food and drink Maine Potato Blossom Festival Five-Mile Road Race A five-mile race through downtown Fort Fairfield during the festival celebrating Aroostook County's potato crop in bloom.
- Novelty course Marshall Point 5K (Marshall Point Lighthouse Loop) A loop of the St. George peninsula that runs past Marshall Point Lighthouse and through the fishing village of Port Clyde.
- Food and drink Moxie Day 5K The road race of Lisbon's Moxie Festival, which celebrates Maine's official soft drink, with Moxie performance shirts for pre-registrants.
- Mud and obstacle Muddy KAT A two-lap muddy 5K at a north-woods lodge near Katahdin, part of a weekend where trail-cleanup volunteers can get free lodging and meals.
- Holiday and seasonal NRCM Polar Bear Dip & Dash A 'warm-up' 5K out to Bug Light lighthouse, then a plunge into the Gulf of Maine off Willard Beach.
- Food and drink Pat's Pizza Clam Festival Classic 5 Mile Run The 43-year-old road race of the Yarmouth Clam Festival, a Maine summer tradition since 1965, starting and finishing on Memorial Green.
- Novelty course Peaks Island Road Race Take the Casco Bay Lines ferry out from Portland, run a 5-mile loop around Peaks Island, then stay for a Downeast lobster bake.
- Animals Save a Stray 5K & Walk Bills itself as Maine's first dog-friendly 5K, run with your pup through Freeport to benefit Midcoast Humane.
- Iconic tradition TD Beach to Beacon 10K Maine's largest road race runs from Crescent Beach to a finish beside Portland Head Light, often called the most photographed lighthouse in the world.
- Mud and obstacle Thomas College Dirty Dog Mud Run A family mud run on a college campus with 12-14 obstacles, plus a lap-racer division that tries to complete as many muddy laps as possible.