As the air turns crisp and the leaves begin to paint the landscape with shades of orange and gold, the charming city of Portland, Maine comes alive with a vibrant array of nearby fairs and festivals that celebrate the essence of autumn. September and October offer a perfect opportunity to explore the local culture, indulge in delicious treats, and revel in the picturesque beauty that defines this region. Let’s take a journey through some of the best fairs and festivals that make fall in Maine truly special.

Maine Crafts Guild’s Scarborough Fine Craft Show (September 16 – 17): For those interested in handcrafted artistry, the Maine Crafts Guild’s Scarborough Fine Craft Show is a must-visit event. Set against the stunning backdrop of the Scarborough Marsh, this fair features the works of skilled artisans showcasing everything from ceramics and jewelry to textiles and woodworking. The event not only offers an opportunity to purchase unique creations but also to engage with the makers and learn about their crafts.

Common Ground Country Fair (September 22-24) The Common Ground Fair in Unity, Maine, organized by MOFGA, is a lively convergence celebrating sustainable living and organic farming. Attendees engage in workshops, relish vibrant displays of local produce, and immerse themselves in talks about eco-conscious practices. This event is around 1.5 hours from Portland and beautifully encapsulates Maine’s agricultural heritage, fostering a strong sense of community and shared values.

Cumberland County Fair (September 24 – 30): Back in Cumberland County, the annual fair provides an immersive experience into Maine’s agricultural heritage. With an emphasis on family fun, this fair features carnival rides, live music, animal exhibits, and traditional fair competitions. It’s an opportunity to step back in time while enjoying modern entertainment and activities.

Damariscotta Pumpkinfest & Regatta (September 30 – October 9): Embracing the whimsical side of autumn, the Damariscotta Pumpkinfest & Regatta celebrates everything pumpkin-related. This unique festival includes events like pumpkin boat races, giant pumpkin weigh-offs, and pumpkin carving competitions. The highlight is the Pumpkinboat Regatta, where intrepid participants paddle across the Damariscotta River in hollowed-out giant pumpkins. It’s a delightful and lighthearted celebration of the fall season.

Fryeburg Fair (October 1 – 8): Venture just over an hour West of Portland to experience one of Maine’s most iconic fall fairs. The Fryeburg Fair, established in 1851, is Maine’s largest fair featuring an amalgamation of agricultural exhibits, thrilling rides, live entertainment, and delectable fair food. Visitors can witness traditional livestock shows, explore craft demonstrations, and enjoy a variety of entertainment options. It’s a quintessential New England fair that captures the spirit of the season.

Harvest Festival at Shaker Village (October 7): Immerse yourself in history and culture at the Harvest Festival held at Sabbathday Lake Shaker Village. This festival offers a glimpse into the past with traditional craft demonstrations, historic tours, and seasonal activities. Attendees can learn about the Shaker way of life, participate in workshops, and enjoy the serene beauty of the village’s surroundings.

Harvest on the Harbor (October 25 – 28): A true culinary delight, Harvest on the Harbor showcases the finest aspects of Portland’s culinary scene. Held at various locations throughout the city, this food and wine festival brings together local chefs, artisans, and beverage producers to offer a unique experience for food enthusiasts. From gourmet tastings to cooking demonstrations, this festival provides a chance to savor the region’s freshest ingredients and indulge in creative dishes.

As the leaves start to fall and the crispness of autumn fills the air, the fairs and festivals around Portland, Maine beckon visitors to partake in a rich tapestry of experiences. From culinary delights to handmade crafts and from playful pumpkin celebrations to agricultural showcases, these events capture the spirit of the season and offer a glimpse into the heart of Maine’s vibrant culture. The fairs and festivals of September and October near Portland have something special to offer for everyone, and The Francis make the perfect home away from home amidst your fall frolicking.