Your Guide to the Top 2023 Fall Events in Maine

Everyone loves a fun festival when autumn rolls around, but you might need a guide to the top fall events in Maine to find the one that sings to you. With brilliant sunshine and dazzling foliage, September and October in the western lakes district hum with excitement.

Beginning with the Poland Spring Heritage Day celebration, a mere 10 minutes from our charming bed and breakfast on Tripp Lake, and winding down with the week-long Fryeburg Fair, the months of September and October brim with activity. Picture crisp apples and sweet cider, bountiful harvests of fresh produce, challenging road races, carnival rides, and artisan crafts. That, in a nutshell, describes a typical fall weekend in Maine.

September 16 | Poland Spring Heritage Day

Free and fun for all ages, prepare to enjoy trolly rides, kids’ games, a petting zoo, and local craft vendors. Free tours of the Poland Spring Bottling Museum and the Maine State Building remain one of the highlights of this annual event.

September 16-17 | Ricker Hill Orchards Annual Artisan Fair

In the town of Turner, Ricker Hill Orchards produces dozens of apple varieties and small-batch ciders on their hillside orchard in the foothills of Maine. The annual artisans fair showcases local artists and crafters and their handmade goods.

September 23-24 | Wallingfords’ Fruit House Annual Artisan Fair

Another fabulous U-Pick apple orchard, the Wallingfords Fair hosts a similar craft event in Auburn, Maine.  Visit their bakery for fresh apple cider donuts, get lost in the corn maze, and step into the backyard to visit the animals.

September 30 | Maine Lakes Brew Fest

Held annually on the last Saturday of September, the Brewfest features craft brewers from around the region. Sample food and brew from dozens of breweries and enjoy the sound of local musicians. Purchase tickets in advance for this popular event.

October 1-8 | Fryeburg Fair

One of the most widely recognized country fairs, the Fryeburg Fair is a legend in its own time. It features agricultural exhibits, carnival rides, harness racing, and quirky competitions like the skillet toss and anvil throw. This fair had its humble beginnings in 1851. Now, as Maine’s largest agricultural fair, upwards of 225,000 people visit to chow down on homemade pizza, pie, fried dough, and specialty foods.

October 8 | Waterford Fall Foliage Road Race

Runners, walkers, and fun run fans flock to the Waterford Fall Foliage Race to test their mettle on this challenging but scenic out-and-back road race. Pre-register for this annual event to receive one of the very popular long-sleeve t-shirts.

October 7-8 | Freeport Fall Festival

Held every year on the first weekend in October, this 3-day festival gathers the best of the best from around the region. Artists, crafters, and food vendors fill the L.L.Bean campus, the Freeport Historical Society grounds, and the Freeport Village Station courtyard. In addition to the exhibits, local musicians entertain from the Discovery Stage with live music.

So, if you plan to take an autumn break this year, add these top fall events in Maine to your calendar. Join us at the Wolf Cove Inn for a relaxing and romantic getaway at our little slice of heaven on Tripp Lake.

Published July 2023