River Jam Dash To The Sea
10 a.m. Saturday, Sept. 15. Front Street Boat Launch, Saco. $15.
A paddle race on the lower Saco River! There are two race course length options: a 4-mile recreational course and an 8-mile competative course. Open to canoes, kayaks and paddleboards. This event is part of River Jam Fest, which takes place Friday and Saturday with music, theater, food, and events.
riverjamfest.com

Paddle + Picnic on the Presumpscot
9 a.m. Saturday, Sept. 15. Shaw Park, Gorham. Free.
Enjoy a leisurely paddle on the Presumpscot River. Bring your own kayak, canoe, or paddleboard to Shaw Park. After the paddle, stick around for a picnic (BYO lunch) and a chance to demo some Hobie Eclipse pedalboards (like paddleboards, but you pedal them). This event is hosted by Fit Maine and the duo behind the guidebook "Paddling Southern Maine." It's free, but food donations to the food pantry at South Portland High School are appreciated!
fitmaine.com

Funky Bow Trail Hop
10 a.m. Saturday, Sept. 15. Funky Bow Brewery, Lyman. $35.
A 5K through the woods near Funky Bow Brewery in Lyman. Run or walk the 5K, then hang out for some beer. The first 150 registrants event get a sweet commemorative glass.
www.funkybowbeercompany.com

Trail to Ale 10K Race + Walk
9 a.m. Sunday, Sept. 16. Eastern Prom, Portland. $35.
Run or walk this popular 10K that follows the Eastern Prom trail to Back Cove. Racers and walkers finish with an after party featuring local beer, pizza, yoga, massages, and a dance party on the beautiful Eastern Promenade. The race supports Portland Trails.
trails.org

The Amazing Chase
8 a.m. Saturday, Sept. 22. Sebago Lakes Region Chamber of Commerce, Windham. $299 per 4-person team.
The Amazing Chase is a team tech adventure race involving a series of challenging team building activities. This adventure involves technology, strategy, finding landmarks, solving clues, trivia, performing tasks, completing physical challenges, and taking photos/videos. Registration deadline is Sept. 14!
amazingchasesebago.com

Ripple Across Portland
9 a.m. Saturday, Sept. 22. $40 registration fee and fundraise $360+.
The first-ever Ripple Across Portland is a team adventure race where teams of 6 will compete in a series of challenges throughout Portland earning points for each activity completed. Some challenges will be easy: say, ask a stranger what their favorite song is and sing it to them. Others will be more difficult, like building your own raft with duct tape, then completing a challenge in Casco Bay. There's an after party and winners get a lobster bake on Cow Island. The event is 21+ and benefits Rippleffect.
rippleacrossportland.org