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4 Reasons to Make for The Maine Highlands This Summer

by Aoife O'Riordan

May 19, 2025

© Suzanne M. AuClair

Destinations / North America

Shake off winter and embrace the warmer days in Maine’s Highlands this summer. If its natural beauty isn’t enough to convince you to make a trip to the area, these three exciting and unique experiences and events might do the trick:

 

Maine Whoopie Pie Festival (June 14)

From 10 a.m. to 4 p.m., this fun festival in Dover-Foxcroft celebrates all things whoopie pie. Sample a variety of whoopie pies, from traditional flavors to unique twists. The event also features vendor stalls, live music, family-friendly games and amusement rides.

 

Americana Music Festival (May 24)

Taking place next to Boreal Theater in Downtown Millinocket, this all-day music festival will feature award-winning country artist Perley Curtis, bluesman Mark “Guitar” Miller, Continental Shakedown, Crow Stew with Steve Bailey Sr., Blue Steel Express and Kevin Kimball. Additionally, Maine’s premier radio DJ Mike Dow will serve as MC. Bring your lawn chairs and enjoy food trucks like Lucy Q’s Place and Bear Mountain Smoke Shack.

 

© Suzanne M. AuClair

 

19th Annual Thoreau-Wabanaki Trail Festival (July 23-28)

Taking place in the Moosehead Lake/Greenville area, this festival honors Transcendentalist Henry David Thoreau’s historic canoe journeys with Penobscot guides. The festival traces traditional Wabanaki routes across the Kennebec, Penobscot and allagash rivers as described in Thoreau’s work, The Maine Woods. Expect nature experiences, thought-provoking talks and immersive sessions on Penobscot traditions.

 

Bass Park After Dark (May 23)

Celebrate the beginning of Memorial Day weekend at this lively event in Bangor, from 4 to 9 p.m. Expect artisan vendors, food trucks and live music. Vendors sell everything from handmade crafts and local goods to tasty food and beverages.

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