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2025 Annual Freeport Fall Festival

Arts and Entertainment

September 13, 2025

From: Freeport Fall Festival

Each year on the first weekend in October, Visit Freeport brings together over 225 of the best New England artists, makers and local food producers for a three-day festival throughout downtown Freeport, Maine.

In addition to browsing local art, join us for three days of live music. There are also plenty of free activities for kids from make ‘n take crafts, to scavenger hunts and more. And, thanks to our generous sponsors, it’s all FREE!

Schedule Of Events

Friday, October 3

Mallard Stage
12:00–12:45 Stone Free. Nostalgic blend of old and new light rock and country hits.
1:15-2:00 Bear Camp Radio. Laid-back indie folk.
2:30-3:15 Becky Krill. Soulful vocals over warm, nostalgic and inspired compositions.
3:45-5:45 Lee Stearns. Acoustic & electric covers.

M.A.D.E. (31 MAIN ST.) Stage
12:00–12:45 Ronnie Mocciola. Slow, sad songs to upbeat foot stompers.
1:15-2:00 Shana Aisenberg & Gale Johnsen. Appalachian, old time, Celtic, New England Contradance, klezmer and more!
2:30-3:15 Krys Beal. Unique and nostalgic blend of old and new top 40’s hits.
3:45-5:45 Andrew Thomas. Piano pop!

Discovery Park Stage
12:00–1:00 Uprise Lite with Sami. An electric playlist, low-impact moves, and a party atmosphere, it’s perfect for beginners, baby-wearers, or anyone with hip or knee issues.
1:30–2:30 Seth Gallant. Folk songwriting and roots music from Milltown New England.
3:00-4:00 Yoga with Live Percussion. Once-a-lifetime musical movement experience with live percussion by talented musician Pete Whitehead will help you reach levels of presence and peace that you hadn’t thought possible.
4:15-4:45 Little Soul Dancers. Kids (ages 2-10) explore what it means to feel at home and happy in their bodies through creative movement, age-appropriate choreography, and games.
5:00-6:00 Family-friendly DJ dance party with Tha Professa

Family Activities
12:00–3:00 Create an oyster shell ornament with Freeport Community Services! - Booth 6 (Town Hall)
3:00–6:00 Face painting. Hosted by the State of Maine Office of MaineCare Services. - Booth 6 (Town Hall)
3:00–6:00 Make dried flower bookmarks with the Freeport Community Library. - Booth 120 (Mallard Parking Lot)
3:00–6:00 Make a craft with the staff of Wolfe’s Neck Center. Booth 119 (135 Main Street)

Saturday, October 4

Mallard Stage
10:00–10:45 Krys Beal. Unique and nostalgic blend of old and new top 40’s hits.
11:15-1:15 John Sayles. Singer, songwriter, guitarist, and producer.
1:45-2:30 Wes Covey. Fingerpicking folksinger.
3:00-3:45 Anna Jones. Blends folk and indie roots with storytelling and folklore.
4:15-6:00 Jack Fossett. Award-winning guitarist, singer and songwriter. Americana

M.A.D.E. (31 MAIN ST.) Stage
10:00–10:45 Pine Ridge Ramblers. Acoustic bluegrass, Americana, and folk music.
11:15-12:00 Anna Jones & Mary Fairfield. Blends folk and indie roots with storytelling and folklore.
12:30-2:30 Ashlyn Bard. Self-therapy through songwriting and storytelling.
3:00-3:45 An Overnight Low. Portland indie pop.
4:15-5:00 Joe Sweeney. Original tunes on ukulele.
5:30-6:15 Backyard Strings. Local favorites!

Discovery Park Stage
10:30–11:15 Uplift with Anne. Feel strong and recharged. A rhythm-based strength experience blending functional resistance training with deep muscular activation.
11:30–12:30 Sigrid Sibley. Singer-songwriter from Maine. Guitar, mandolin & vocals.
1:00-1:30 Little Soul Dancers. Kids (ages 2-10) explore what it means to feel at home and happy in their bodies through creative movement, age-appropriate choreography, and games.
2:00-4:00 Red Tail Hawk. Vibrant fusion of alternative, groove rock and pop. Soaring melodies, heady grooves and high-energy performances that have earned them distinction on Boston’s north shore.

Family Activities
10:00–2:00 Local artists will work with kids to create a fun take home art piece. Hosted by Meetinghouse Arts. Booth 6 (Town Hall)
10:00–6:00 Meet the Freeport Lionesses and create! Make a free craft to take home. - Booth 120 (Mallard Parking Lot)
10:00–6:00 Kids are invited to get their hands dirty! Hosted by Coastal Maine Botanical Gardens. - Booth 119 (135 Main Street)
11:00–3:00 Meet adoptable pups from New England Lab Rescue! – Find them on the lawn near the stone pillars. (Town Hall)
2:00–4:00 Families are invited to visit Sweetser’s gigantic game station with cornhole, skee ball, and giant connect four. - Booth 6 (Town Hall)

Sunday, October 5

Mallard Stage
10:00–12:00 Paddy Mills. Award-winning folk singer/songwriter whose songs are as salty as the Maine coast he calls home.
12:30-1:15 Wes Covey. Fingerpicking folksinger.
1:45-2:30 Trisha Mason. Downeast singer & songwriter.
3:00-3:45 Becky Krill. Soulful vocals over warm, nostalgic and inspired compositions.

M.A.D.E. (31 MAIN ST.) Stage
10:00–10:45 Doug Kolmar. Explores the beauty and trouble of our inner and outer worlds with compassion, wit, and insight.
11:15-12:00 Trisha Mason. Downeast singer & songwriter.
12:30-1:15 Alice Limoges. Strong folk-style voice on original songs.
1:45-3:45 Sorcha Cribben-Merrill & Chris Robley. Americana and indie-pop songs. Folk/pop/soul covers.

Discovery Park Stage
10:30–11:15 Pilates with Nicolle. Move through more traditional exercises rooted in Pilates precision, perfect for anyone seeking impact-free intensity or who’s looking for a balance to our higher-intensity classes.
11:30–12:15 STEP UP. Beat-based blend of step aerobics, hip-hop, Afrobeat, and dancehall, with choreography that’s playful (but never intimidating) and music that makes it impossible not to move.
12:30-2:30 Mike Wallingford. Guitar & vocals.
1:30-2:30 Benny Z. Original music inspired by nature; guitar, cello, and vocals.
3:00-4:00 Emily Sclar & The Galaxy. Maine native. Live string band.

Family Activities
10:00–1:00 Local artist instructors will work with kids to create something special to take home. Hosted by ArtVan. Booth 6 (Town Hall)
10:00–4:00 Use rainbow breathing to make a bracelet or keyring. Hosted by Girl Scouts of Maine, Travel Sisters Troop. Booth 120 (Mallard Parking Lot)
10:00–4:00 Kids are invited to get their hands dirty! Hosted by Coastal Maine Botanical Gardens. - Booth 119 (135 Main Street)
1:00–4:00 Get creative with the Center for Arts & Ecology at the Desert of Maine. – Booth 6 (Town Hall)

Date and Time

Friday, October 3, 2025
12pm - 6pm

Saturday, October 4, 2025
10am - 6pm

Sunday, October 5, 2025
10am - 4pm

Locations:
L.L.Bean Discovery Park
Mallard Parking Lot (Behind Freeport Historical Society) 
Freeport Village Station
135 Main Street (former KeyBank lawn) 
Freeport Town Hall (including the MADE Parking Lot)

Freeport, ME

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