Shannon Bryan from FitMaine.com loves costumes. And doing things. And now she's combined those two passions.
Sunday, October 23, 3-6 p.m. Meet in Monument Square, Portland. Free.
I look forward to this event every year for two reasons: First, it’s a splendid leisurely bike ride through Portland with a photo stop at Deering Oaks. Second, it’s the perfect opportunity to bust out some old-timey attire and look oh-so-dapper for all the world to see.
Halloween at EVO
5 to 10 p.m Friday, October 28. EVO Rock + Fitness, Portland. Free! (So long as you’re in costume!).
Dress in costume, climb for free at EVO Rock + Fitness! (Be a spider! It’d be hilarious! Or a lizard!) There will be a costume contest, of course, along with prizes, games, and the chance to win a free membership. Plus headlamp climbing from 7-10 p.m.
10 a.m. Saturday, October 29. Meet at boat ramp at Bug Light Park, South Portland. Free.
Don't put that paddleboard away just yet! The annual Halloween paddle is a chance to take to the waters of Portland Harbor - in costume! - before the cold weather really kicks in. Costumes encouraged. Wetsuits recommended. PFDs and leashes required!
Bike & Brews
11 a.m. to 2 p.m. Saturday, October 29. Starts and ends at Elsmere BBQ, South Portland. $20.
The final installation of Bikes and Brews is on October 29, which is gloriously close to Halloween. Last year, some riders wore costumes, so organizers are encouraging it again this year!
Freaky 5K run/walk
10 a.m. Saturday, October 29. Colby College’s Field House, Waterville. $25 for adults and $15 for students in advance, $35 for adults and $25 for students day of race.
The costume contest begins at 9:45 am. Prizes will be awarded for scariest, most creative and best team costumes. And a “hardiest” category for costumes that “highlight a ruckus causer.” A benefit for Hardy Girls Healthy Women!
Dispatch Magazine Halloween 5k Road Race
11 a.m. Sunday, October 30. Back Cove, Portland. $15.
Back Cove is a popular place to run for folks in the greater Portland area. It’s supremely pretty (and nice and flat, too)! But this Halloween-inspired race encourages participants to compete in costume, which makes it a sight you likely haven’t seen, no matter how many times you’ve run Back Cove before.