Fall Kickoff Weekend in Downtown Easton: A Celebration of Art, Autumn, and Community
The charming brick sidewalks and vibrant streets of Downtown Easton are getting ready for one of the most anticipated events of the year — the Fall Kickoff Weekend, taking place Friday, October 3rd and Saturday, October 4th, 2025. This year’s celebration promises to be the biggest and most festive yet, packed with art, music, family fun, and, of course, pumpkins galore!
Stroll the Pumpkin Trail
Get ready for a pumpkin-packed weekend as local businesses throughout downtown Easton showcase giant, professionally carved pumpkins in their storefronts. Each one is uniquely decorated with fall themes, pop culture icons, and artistic flair. Visitors are encouraged to take a leisurely walk along the Pumpkin Trail and snap photos of their favorites. It’s the perfect way to celebrate the season and support local shops.
Family Fun & Creative Activities
Over at the Academy Art Museum (AAM), the weekend is brimming with activities for kids and families:
- Pumpkin Painting: Children can decorate their very own pumpkins to take home! Available both Friday and Saturday from 10 AM to 2 PM.
- Outdoor Movie Night: Friday evening, bring a blanket or chair and enjoy a free screening of Monster House under the stars in AAM's charming outdoor setting.
Meanwhile, the Talbot County Free Library will be hosting fall-themed crafts and activities for kids on Saturday from 10 AM to 2 PM — a great stop for little ones and families!
Downtown Easton will be alive with the sounds of the season all weekend:
Friday, October 3rd:
- Cascading Carlos, the dynamic juggler and entertainer, will amaze audiences in Thompson Park from 5 PM to 7 PM.
- Enjoy live music performances as you explore the streets and stores of Easton.
Saturday, October 4th:
- Honey Sol takes the stage from 11 AM to 3 PM
- Madisun Bailey will follow from 3 PM to 7 PM, adding soul and energy to your Saturday stroll.
First Friday Gallery Walk & Special Exhibits
October's First Friday Gallery Walk (October 3rd) is the perfect time to explore the town’s incredible art scene. Visit local galleries such as:
- Studio B Gallery
- The Trippe Gallery
- Troika Gallery
- Spiralis Gallery
- The Zebra Gallery (featuring Boardwalk Fare, a polymer clay exhibit by Joseph Barbaccia with DJ Hector)
- TRA Gallery, Zach Gallery, The Market at Dover Station, 9S Studios, and more!
Don’t miss “Pretty in Pink,” a special fine art sale hosted by the Working Artists Forum at 40 South Harrison Street. This meaningful event supports Breast Cancer Awareness Month, with proceeds benefiting the Clark Comprehensive Breast Center. Join the celebration Friday from 4 PM to 8 PM and Saturday from 11 AM to 4 PM.
Shop, Dine & Explore
Easton’s unique retailers and restaurants are rolling out the red carpet for Fall Kickoff Weekend:
- Enjoy exclusive autumn sales from your favorite shops.
- Savor seasonal tasting events and food & drink specials.
- Experience live performances while enjoying local flavors.
With over 80 shopping, dining, and entertainment venues, downtown Easton offers something for everyone. Whether you're a local or visiting for the weekend, you're sure to fall in love with all that our town has to offer.
So mark your calendars, grab your cozy sweater, and head to Downtown Easton for a weekend filled with art, music, pumpkins, and community spirit. It’s going to be a fall celebration you won’t want to miss!
