Fall into Fun: Must-Visit Festivals and Events in the Area - Holiday Inn by the Bay

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Fall into Fun: Must-Visit Festivals and Events in the Area

As the crisp autumn breeze sweeps through the coastal city of Portland, Maine, it’s time to embrace the vibrant colors, warm apple cider, and the enchanting fall festivals that make this season truly special. From lively fairs to charming pumpkin festivals, the Holiday Inn By The Bay is your gateway to an unforgettable fall experience. Join us as we highlight some of the most exciting events happening in the area, including the Freeport Fall Festival, Fryeburg Fair, Cumberland County Fair, Camp Sunshine Pumpkin Festival, Hurricane Meadows Fall Festival, Pineland Farms Harvest Festival, and Shaker Village Harvest Festival.

Freeport Fall Festival

freeport fall festival

photo via Visit Freeport

Kickstarting the fall festivities in the area, the Freeport Fall Festival promises a delightful weekend of arts, crafts, music, and delicious food. Stroll through the historic streets of Freeport, just a short drive from our hotel, and discover unique handcrafted goods, enjoy live entertainment, and indulge in mouthwatering treats. Don’t forget to check out the local shops and take home a piece of Maine’s artisanal charm.

Fryeburg Fair

fryeburg fair horse racing

photo via Facebook

Venture inland to Fryeburg, where the Fryeburg Fair has been a cherished tradition for over 160 years. This agricultural extravaganza boasts everything from thrilling rides to farm animal exhibits. Savor classic fair foods, explore arts and crafts, and experience the excitement of harness racing. A short scenic drive from Portland, this fair is a must-visit for those seeking an authentic taste of rural Maine.

Cumberland County Fair

photo via Facebook

The Cumberland County Fair offers family-friendly fun just moments away from the Holiday Inn By The Bay. Enjoy carnival rides, live entertainment, and a variety of food vendors. This fair celebrates Maine’s agricultural heritage and is the perfect place to create lasting memories with loved ones.

Camp Sunshine Pumpkin Festival

pumpkin festival

photo via Facebook

Support a heartwarming cause at the Camp Sunshine Pumpkin Festival in nearby Freeport. This event brings the community together to celebrate fall and raise funds for families dealing with life-threatening illnesses. Illuminate the night with carved pumpkins, enjoy live music, and partake in delicious food options, all while contributing to a meaningful cause.

Hurricane Meadows Fall Festival

hurricane meadows fall festival

photo via Hurricane Meadows

For a dose of rustic charm, make your way to Hurricane Meadows Fall Festival in Falmouth. This local gem offers a true taste of Maine’s countryside, complete with a sunflower field, pumpkin picking, corn pit, potato cannon, pie pumpkin basketball, a corn maze, and more. It’s a perfect outing for families and those seeking a laid-back fall experience.

Pineland Farms Harvest Festival

pineland farms corn maze

photo via Facebook

Indulge in the beauty of New Gloucester’s Pineland Farms during their Harvest Festival. This event showcases the best of rural Maine with a corn maze, pumpkin patch, and apple cider demonstrations. Don’t miss the chance to savor fresh apple cider—a quintessential fall experience.

Shaker Village Harvest Festival

shaker village harvest festival

photo via Shaker Village

Immerse yourself in history and culture at Sabbathday Lake Shaker Village’s Harvest Festival. Located just a short drive from Portland, this event offers a unique blend of traditional craft demonstrations, wagon rides, live music and food. Explore the beautiful Shaker buildings and witness the vibrant fall foliage surrounding this historic site.

As autumn leaves paint the landscape with shades of red and gold, the Portland, Maine area comes alive with fall events and festivals. Whether you’re seeking the thrill of a fair, the charm of a pumpkin festival, or the tranquility of a rural retreat, there’s something for everyone. And when you stay at the Holiday Inn By The Bay, you’re just moments away from all the fall fun. Don’t miss the chance to make unforgettable memories and experience the best of fall in Maine.

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