Fall KickOFf weekend
Welcome to Fall!
The brick sidewalks and bustling streets of Downtown Easton are preparing to play host to the town’s Fall Kickoff Event on October 3th and 4th, which promises to be bigger than ever this year!
You can bet your Autumn dollar that it will be a fun time for all!
As in previous years, various businesses throughout downtown Easton will have giant pumpkins professionally carved and decorated in their storefronts, depicting fall themes, pop culture, and more. Visitors are encouraged to stroll through town and take pictures of their favorite pumpkin along the pumpkin trail!
The Academy Art Museum will host pumpkin painting for children to decorate and take home. AAM will also host the fall outdoor movie night with a free showing of Gil Kenan’s Monster House. Attendees are encouraged to bring a blanket or chairs as they enjoy the cozy, historic atmosphere during the feature film. Local bands will be playing live in several areas, as well as phenomenal juggling demonstrations from professional juggler and entertainer Cascading Carlos.
While downtown comes alive with activity, Easton’s shops and unique retailers will welcome all visitors with special sales and savings for the autumn season. Local restaurants will also host tasting events, food and drink specials, as well as live performances. With around 80 shopping, dining, and entertainment venues, downtown Easton will be filled with autumnal fun and picture-perfect art for everyone to experience.
Fall Kickoff Weekend is made possible by the generous support of signature sponsor Preston Automotive Group, Bay Country Security and Safehouse LLC, the Town of Easton, and the Easton Economic Development Corporation.
Live Sculpture Demonstrations
Friday Night from 5 pm to 7 pm
The featured attraction of the kickoff is the on-site carving of pumpkins along the giant pumpkin trail. You’ll have a chance to see the artists from Icelab work their magic as giant gourds become amazing works of art! There will be 3 live carvings sprinkled throughout downtown Easton on Friday evening. See if you can catch them all! The first live carving will be at 5:00pm at Tiger Lily located at 206 N Washington Street. The second live carving will be in front of the Talbot County Courthouse located at 11 N Washington Street at 6:00pm and the third and final live carving with be at the Waterfowl Building located at 40 S Harrison Street at 7:00pm.
Friday Evening
Giant pumpkin trail and fall festivities!
Enjoy a live musical performance fom Poppy Blue Eyes from 4 pm to 7 pm and outdoor entertainment during the first night of kickoff!
Cascading Carlos will be in Thompson Park from 5 p.m. to 7 p.m! Carlos has fascinated and entertained children and adults alike for over two decades with his phenomenal juggling demonstrations and terrific personality.
October’s First Friday Gallery Walk will also be the perfect opportunity to find incredible, vibrant pieces from an array of talented artists. Whether you visit Studio B Gallery, The Trippe Gallery, Troika Gallery, Spiralis Gallery, The Zebra Gallery, The Zach Gallery, The Market at Dover Station, 9S Studios, Wittersgreen, and the TRA Gallery, your eyes are in for a visual feast.
The Zebra Gallery will host Boardwalk Fare, a art exhibit featuring polymer clay paintings by Joseph Barbaccia. The opening will also have music provided by DJ Hector.
The Working Artists Forum and special guests invite you to attend Pretty in Pink, a fine art sale on Friday, October 3rd, 2025, from 4:00 pm to 8:00 pm at 40 South Harrison Street. This free event honors Breast Cancer Awareness month with proceeds to benefit the Clark Comprehensive Breast Center. Join the WAF for a day of art, music, information, and refreshments with free admission and celebrate Pretty in Pink in Easton.
The Academy Art Museum will also host pumpkin paintings for children to decorate to take home. AAM will also host the fall outdoor movie night with a free screening of Gil Kenan’s Monster House. Attendees are encouraged to bring a blanket or chairs as they enjoy the cozy, historic atmosphere while watching the film.
While downtown comes alive with activity and the feeling of seasonal warmth, Easton’s shops and unique retailers will welcome all visitors with special sales and savings for the autumn season. Local restaurants will also host tasting events, food and drink specials.. With around 80 shopping, dining, and entertainment venues, downtown Easton will be filled with autumnal fun and picture-perfect art for everyone to experience.
Saturday
Live musical performance from Honey Sol from 11 am to 3 pm & Madisun Bailey from 3 pm to 7 pm
The joyful fall fun continues on Saturday!
The Talbot County Free Library will host free fall-themed activities for kids from 10 am to 2 pm. The activities are free for all! Two Pair Collectibles, Be With Me Playseum, the Easton YMCA, and Talbot Humane will offer various fun activities for all visitors!
Pretty In Pink will also continue into Saturday from 11 am to 4 pm. Stop by 40 South Harrison Street for an amazing gallery of fine art!
The Academy Art Museum will also host more pumpkin painting from 10 am to 2 pm.
Fall Kickoff Information
Check out our listings below to help plan your weekend!