Invite 106 // Oct 29

By the time I shut my laptop, the sun was already dipping below the hills outside Portland. Rejecting the circadian urge to stay inside where it's light and warm, I grabbed a headlamp, bright orange vest, and my mountain bike and headed for the trails.

I switched on my headlamp as I approached the summit, pausing at the top to enjoy the stillness and quiet. My steamy breath drifted in the light beam toward the crunchy oak leaves hanging above me.

The ride down was total silence. The shadows were long. It was spooky in a way that reached my inner child and made me pedal faster.

Shoulder season gets a bad rap. Too dark, too cold, caught awkwardly between the good parts of the year. But that misses what the season offers: crunchy leaves lit by headlamp, the kind of quiet that makes you hold your breath, shadows long enough to spook your inner child. It's not vibrant like summer or powdery like winter, but it's novel, immediate, and fun, and that's enough

Happy autumn, Outsiders. Now on to the good stuff.

✌️ Max

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Portland Bike Party: Halloween Ride

Fri, Oct 31 | Portland | Free

Dress up and pedal through Portland on a Halloween-themed bike ride, enjoying the festive atmosphere and community spirit. (Keep an eye on the weather)

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Baxter 5k Relay Race

Sat, Nov 1 | Auburn | Paid

Compete in a 5km relay or tackle the course solo at Lost Valley, winding through scenic trails and concluding at the base lodge, with the Backyard Beer Festival happening nearby.

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Quarry Road Fall Festival

Sat, Nov 1 | Waterville | Free

Celebrate fall at Waterville's go-to trail system with outdoor activities like a campfire and s'mores, a scavenger hunt, and pumpkin bowling.

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Long Pond Community Sauna

Sun, Nov 2 | Mount Desert | Paid

Experience the warmth of a community sauna at Long Pond on MDI, where you can relax with friends or enjoy a quiet moment overlooking the water.

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Live Well 5k

Sun, Nov 2 | Portland | Free

Lace up for a community-focused sober run/walk around Back Cove in Portland, offering a supportive atmosphere for all fitness levels.

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Wildlands Summit Run

Sun, Nov 2 | Orland | Free

Tackle a 6.2-mile trail run or walk to the summit of Great Pond Mountain, hosted by the Great Pond Mountain Conservation Trust, with a fun run option for all ages.

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November Full Moon Dip

Thu, Nov 6 | South Portland | Free

Extend the beach season and join Two Maine Mermaids for their next monthly group dip at Willard Beach.

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Turkey Ride

Sat, Nov 15 | Rockport | Donation Based

Cycle from Maine Sport in Rockport to Hannaford for turkey pickups, then donate to the Camden Area Food Pantry before returning for post-ride snacks.

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Millinocket Marathon & Half

Sat, Dec 6 | Millinocket | Donation Based

Register today for one of Maine's most unique events, featuring a free grassroots race in the foothills of icy Katahdin to celebrate Millinocket's community spirit.

Learn more

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Coming Up (Previously Featured)

Slow Leaf Peeping Class | Sun, Sep 14 - Sun, Nov 2 | Paid

Pumpkin Hike | Wed, Oct 29 | Free

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Trail Log: Share your Experience

Have you attended any of these recent activities? Use the quick check-in links(30 seconds or less) to log your attendance and share your experience.

📝 Pumpkin Patch Trolley - Fri, Sep 26 - Sun, Oct 19

📝 Presumpscot River Revival Race - Sat, Oct 18

📝 Haunted Tides - Sat, Oct 18

📝 Gear Again Festival - Sat, Oct 18

📝 Bike & Brew on the Eastern Trail - Sat, Oct 18

📝 Wolfe's Neck Fall Festival - Sat, Oct 18

📝 North Head Hike and Pizza - Sat, Oct 18

📝 Run MDI: Mount Desert Island Marathon, Half & Relay - Sun, Oct 19

📝 Historical Hike: The Great Disappointment of 1844 - Wed, Oct 22

📝 Beach Plum Pursuit - Fri, Oct 24 - Sun, Oct 26

📝 Thorne Head Trail Run - Sat, Oct 25

📝 Lost Valley Fall Fest - Sun, Oct 26

Your responses help us decide which events to feature again and motivate the newsletter's continued creation.

👋 I'm Max. I created the Maine Outsider to help people connect with organizations offering outdoor events and experiences around the state.

I monitor 300+ newsletters, but can't know everything. If you're hosting an event or have a tip about an upcoming experience, use our tip line to let me know.

Thanks for reading. Now, get out there!

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