Portland has a lot of upcoming races to look forward to – what better way to get motivated than to sign up for a few?
May 5: It’s 5 O’Clock Somewhere 5K
Time & Place: 5 p.m. Freeport
After your run, enjoy a bonfire at Gritty McDuff’s Brew Pub. Your registration includes a beverage and collectible mug to drink with. The run benefits Habitat for Humanity’s Women Build Project.
May 19: GORUCK Challenge Adventure Race
Time & Place: 1 a.m. Portland
This race is a team event led by Green Berets that takes 8 to 10 hours and covers 15 to 20 miles. The route isn’t unveiled until the week of the event. You need to be prepared for this by bringing the right supplies (there’s a list of necessities online). Bring some friends – this is quite the challenge!
Time & Place: 8:15 a.m. Point Sebago Resort, Casco
Who doesn’t love pirates? This theatrical race includes a pirate ship, costumes, and more during the 1/3 mile swim, 14-mile bike and three-mile run event.
June 14: The Twilight 5K Road Race
Time & Place: 7 p.m. Southern Maine Community College, South Portland
Stunning sunset views, this race supports the Maine Cancer Foundation.
June 24: Bands on the Run Half Marathon & 5K
Time & Place: 8:30 a.m. Simard Payne Park, Lewiston
Six bands will be located along the race courses to entertain both runners and spectators. This will be a lot of fun!
July 22: Shipyard Old Port Half Marathon & 5K
Time & Place: 7:30 a.m. Portland
Finish your run with a Shipyard beer garden on Maine State Pier. Great views!

Figures I would learn of this event, but also find out I cannot run for almost another 10 months after Achilles tendon surgery (insert your squeemish sigh here).
Sunday, October 4, beginning at Simard-Payne Police Memorial Park in Lewiston, 3,500 registered cyclists, runners, and walkers will participate at various distances in The Dempsey Challenge, a wonderful charitable event in Lewiston-Auburn, Maine. Registration is currently closed at the cap of 3,500 entrants in the biking, running, and walking events, however, they are still accepting “virtual riders” who can still raise funds. The Dempsey Challenge fundraiser will benefit The Patrick Dempsey Center for Cancer Hope & Healing, the brainchild of the Hollywood actor and Lewiston, Maine native, who knows personally how support and care giving services can directly impact the healing of cancer patients, as his mother is a four-time ovarian cancer survivor.
Portland, Maine, has a very active running community, which is why on any given day of the year you will see your fair share of novice to die hard runners (they will run in virtually any weather), joggers, and road racers all around Greater Portland.