Autumn Adventures in Maine | Top Fall Festivals & Seasonal Events 2025

🍁 Autumn Adventures in Maine: Festival Season Is Calling

Maine’s fall foliage is world-famous, drawing visitors from across the globe to witness the breathtaking display of fiery reds, golden yellows, and burnt oranges. But autumn in the Pine Tree State is about more than just the leaves—it’s also festival season and autumn adventures in Maine await!

From county fairs and craft markets to quirky celebrations like pumpkin boat regattas and pirate invasions, Maine in September comes alive with community spirit, fresh harvest flavors, and fun for the whole family. Whether you’re looking for live music, craft beer, agricultural showcases, or seaside traditions, there’s a festival for you.

🌟 Why Visit Maine in September?

• Peak foliage season begins – brilliant reds, oranges, and yellows

• Cool, crisp weather perfect for hiking, biking, and exploring

• Fewer crowds than peak summer season

• Locally made food & crafts at nearly every festival

Here’s your ultimate guide to Maine’s September Fall Festivals—mark your calendars and plan your trip!

📌 Quick Festival Reference Table

Festival	Location	2025 Dates	Website	Contact
Blue Hill Fair	Blue Hill	Aug 28 – Sept 1	bluehillfair.com	(207) 374-3701
Camden Windjammer Festival	Camden	Aug 29 – Sept 1	camdenwindjammerfestival.org	(207) 236-4404
Common Ground Country Fair	Unity	Sept 19–21	mofga.org	(207) 568-4142
Trails End Festival	Millinocket	Sept 19–21	trailsendfestival.org	(207) 723-4443
Eastport Pirate Festival	Eastport	Sept 5–7	eastportpiratefestival.com	(207) 853-4343
Cumberland County Fair	Cumberland	Sept 21–27	cumberlandfair.com	(207) 829-5531
Freeport Fall Festival	Freeport	Sept 27–29	visitfreeport.com	(207) 865-1212

🌾 Blue Hill Fair | Blue Hill, Maine

📅 Labor Day Weekend (Aug 28 – Sept 1, 2025)Since 1891, this iconic Down East agricultural fair has entertained with sheepdog trials, a demolition derby, midway rides, and top-notch live music.

Quick Tip: Come hungry—the fair food here is legendary!

📍 Location: Blue Hill Fairgrounds, 233 Ellsworth Rd, Blue Hill, ME

⛵ Camden Windjammer Festival | Camden, Maine

📅 Labor Day Weekend (Aug 29 – Sept 1, 2025)Celebrate Maine’s maritime heritage as majestic windjammers sail into Camden Harbor. Enjoy the chowder challenge, lobster crate races, treasure hunts, and a nautical dog show.

Quick Tip: Don’t miss the parade of sail when the fleet arrives—it’s picture-perfect!

📍 Location: Camden Harbor, Camden, ME

🌻 Common Ground Country Fair | Unity, Maine

📅 Sept 19 – 21, 2025Hosted by the Maine Organic Farmers and Gardeners Association (MOFGA), this celebration of rural living and sustainability includes 1,000+ exhibitors, workshops, live music, and a bike valet service.

Quick Tip: Ride your bike to the fair—then join the Bike Parade twice daily!

📍 Location: MOFGA Fairgrounds, 294 Crosby Brook Rd, Unity, ME

🎶 Trails End Festival | Millinocket, Maine

📅 Sept 12 – 14, 2025Celebrate the end of the Appalachian Trail with three days of free live music, a chili cook-off, parades, rubber duck races, and outdoor fun in the shadow of Mount Katahdin.

Quick Tip: Join the All Trails Lead to Katahdin Parade—ATVs, canoes, hikers, and Jeeps all welcome!

📍 Location: Downtown Millinocket, ME

🏴‍☠️ Eastport Pirate Festival | Eastport, Maine

📅 Sept 5 – 7, 2025Ahoy, matey! Eastport transforms into a swashbuckling town of pirates, parades, scavenger hunts, and street performers. A family-friendly favorite with music, food, and plenty of costumes.

Quick Tip: Dress like a pirate—it’s highly encouraged!

📍 Location: Downtown Eastport, ME

🎡 Cumberland Fair | Cumberland, Maine

📅 Sept 21 – 27, 2025Running strong for over 150 years, the Cumberland Fair is a staple of Maine’s fall season. Enjoy rides, agricultural showcases, maple sugar house tastings, a demolition derby, and harness racing.

Quick Tip: Visit the Farm Museum for a glimpse into Maine’s farming heritage.

📍 Location: Cumberland Fairgrounds, 197 Blanchard Rd, Cumberland, ME

🎨 Freeport Fall Festival | Freeport, Maine

📅 Sept 26 – 28, 2025Held on the L.L. Bean campus, this free event features 200+ artists and crafters, delicious food vendors, live music, and family-friendly activities.

Bonus: Stick around in October for the Camp Sunshine Pumpkin Festival—thousands of pumpkins light up downtown Freeport!

📍 Location: L.L. Bean Campus, 95 Main St, Freeport, ME

🍂 Plan Your Perfect Maine Fall Festival Trip

From the coastal harbors of Camden and Eastport to the mountain towns of Millinocket and Unity, Maine’s September festivals capture the state’s spirit: community, culture, and natural beauty. Pair your festival fun with a scenic drive, a leaf-peeping hike, or a cozy inn stay for the ultimate fall getaway.

👉 Don’t just see the foliage—celebrate it at a Maine festival!

What to Do in the Moosehead Lake Region & Beyond: Your Complete Guide to Outdoor Adventure & Local Attractions

Planning a trip to the Moosehead Lake region in Maine? You're in for an unforgettable experience packed with adventure, breathtaking natural beauty, and cozy lodging options. From high-adrenaline ATV trails to peaceful paddles on glassy waters, the Moosehead Lake area is a four-season playground perfect for outdoor lovers, families, and anyone looking to unplug and explore.

Want more insider tips? Discover top recommendations at Moose River Lookout, your go-to resource for:

• 🛶 Boating & paddling routes

• 🎣 Fishing hotspots

• 🏕️ Wilderness camping sites

• 🥾 Trail maps for hiking & nature walks

• 🍽️ Local dining & shopping recommendations

👉 Stay Connected with Moosehead News & More!

• Stay updated with the latest happenings and news in the Moosehead Lake region. Learn more about what to do and where to go in the Moosehead Lake area and beyond.

🏡 Where to Stay: Moose River Lookout – Your Basecamp for Adventure

Located in Rockwood, Maine, Moose River Lookout is the ultimate vacation home rental for adventurers and nature lovers alike. Nestled on the Moose River, this cozy home features:

• Private Dock with access to Moosehead Lake

• 3 Bedrooms | 2 Baths | Sleeps 7

• Free WiFi & TV

• Backup Generator

• Easy driveway access for trailers & ATVs

• Direct access to ITS66 Snowmobile Trails

• Year-round availability for summer AND winter sports

Whether you're hiking Blue Ridge, casting a line in the river, or hitting the snowmobile trails—Moose River Lookout is where your Maine vacation begins.

Ultimate Outdoor Getaway

With direct backyard access to Maine's Interconnected Trail System (ITS66) and a private dock on the river, adventure awaits right outside your door. Whether you're into hiking, golfing, boating, fishing, hunting, skiing, or snowmobiling, you'll find it all just steps away from our doorstep.

Book Your Stay

Experience the ultimate outdoor getaway in the heart of Maine's natural beauty. For inquiries or to make a reservation, please don't hesitate to contact us. We look forward to welcoming you to Moose River Lookout, lodging Rockwood Maine a Vacation Home Rental, on Moose River with access to Moosehead Lake and Mt. Kineo!

• Phone: 800-544-0300

• Email: mooseriverlookout@gmail.com

• Address: 4054 Rockwood Rd Rockwood, ME 04478

• Website: Moose River Lookout

Whether you’re looking for live music, craft beer, agricultural showcases, or seaside traditions, there’s a festival for you.