October Events
Crisfield Arts & Entertainment District
Pumpkin Scavenger Hunt – Walk Maryland Day
October 1, 2025, from 3-6 PM
4053 Hinman Lane, Crisfield, MD (across the street from Marion Pharmacy)
Join in celebrating Walk Mayland Day and the beginning of WALKTOBER with a Free Pumpkin Scavenger Hunt. Walk along the trail and find a pumpkin. When you are done walking, bring the pumpkin back to the registration table and claim your prize. One pumpkin per person.
Carve Diem! Seize the Pumpkin!
Join in our online Pumpkin Carving contest. To enter, just snap a picture of your gourd-geous entry and tag on Facebook or Instagram. Submission dates: October 1-17th. Online voting dates: October 18 – 24th. Winners will be announced on October 25th. Prizes awarded at W Main St Gallery: 1-3 PM.
Shrimp Night at the Legion
Friday, October 3, 2025
American Legion
126 Lorrie Quinn Drive, Crisfield, MD
Open to the Public! Join us every first Friday of the month for hot steamed shrimp, clams and hush puppies! Support our veterans and families!
Jazz on the Waterfront
Saturday, October 4, 2025
4-8 PM
Crisfield City Dock
Introducing the 2025 JOTW line-up: saxophonist Fostina Dixon, vibraphonist Joe Baione, bassist Elwood Bishop, vocalist Ronnie Sterling, and vocalist Vaneisa, MC. Come for a musical smorgasbord including some smooth and straight up jazz, a little R&B & a side of blues.
Our musical chefs are saxophonist Fostina Dixon, vibraphonist Joe Baione, bassist Elwood Bishop and vocalists Ronnie Sterling and “Vaneisa” our mistress of ceremony.
Bring a chair. Or purchase a table for 8. Or enjoy a crab feast just before being carted down to the dock.
$40 bring your lawn chair
https://buy.stripe.com/28EeVe06v6Sm1NCfwg5AQ00
$400 table/chairs of 8 (Limited #)
https://buy.stripe.com/14AdRadXl4Ke2RG97S5AQ02
VIP crab feast tkts thru Crab Place
https://www.crabandcruise.com/shop-detail...
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Crisfield! What a great place to be!
Come for the crabs and stay for the sunsets!
Janes Island State Park – Nature Center
Summer Nature Art Wall
Art of local artists is displayed on the wall in the Nature Center. Visit Janes Island State Park for the viewing of art.
Gallery 413 Fall Art Show
Reception: September 26, 2025
Gallery 413
413 W Main St, Crisfield
The Gallery’s Fall Art Show starts on September 26th with an opening reception. This is a free event with refreshments and adult beverages. Go to crisfieldartssyndicate.org for more information on how to submit art for this show. Art submission forms can be found at Gallery 413 and online at: crisfieldartssyndicate.org
Uncorked: Crisfield Waterfront Wine Festival
October 11, 2025, 12-5 PM
Somers Cove Marina
715 Broadway, Crisfield, MD
Art & Craft Vendors, Food Trucks, Beer & Cocktails, Live Music, Wineries
Tickets General Admission $35 (includes unlimited samples)
Corbin Gallery Featured Artist – Jackie Miller
“My Favorite Paintings” on display October 1 – 31st
Opening Reception: Saturday, October 11, 2025, 6-8 PM
Corbin Studio & Gallery
4 E Main St, Crisfield, MD
Lifting Hands Together Christian Concert
October 25, 2025, from 1-10 PM
Crisfield High School
210 N Somerset Ave
Crisfield, MD
To bring people & families together to celebrate first our Lord Jesus Christ, secondly, to share the story of a wonderful Christian man who devoted his entire life to his family, community, and spreading the goodness of God!!!
This will be an all-day event with local and national singers, bands, and choirs performing praise songs we all know. There will be powerful words of testimony, kids’ activities, and food vendors that will hopefully bring people from all over to share this day.
All proceeds for this event will go to a local student scholarship attending a field of Ministry!
Annual Kids Halloween Parade
October 25, 2025, 3-4:30 PM
This year’s Halloween Parade will start at the Tawes Museum and end at the Crisfield Area Chamber of Commerce. Sign up: 410-968-2500 or office@crisfieldchamberofcommerce.com
Wearable Art Workshop with host Montse Tlalolini
October 28, 2025, 5:30 – 7:30 PM
Corbin Studio & Gallery
4 E Main St, Crisfield, MD
Participants will learn to make their own jewelry pieces using wire and natural gemstones. No experience is necessary. It’s designed for ages 12+, but younger children can join with adult supervision, as they may require more guidance. $20 per person, all materials included. Guests will make either a pendant or a set of earrings.
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Now October 25th


MARK YOUR CALENDARS...
Our popular ANNUAL EVENTS!
Start getting excited for the 2026 Summer by planning your stay in Crisfield for our upcoming annual events:
Stars and Stripes Fest
Wheels on the Waterfront
BIG Little Townfest
National Hard Crab Derby: Labor Day Weekend
Tawes Crab and Clam Bake: September 23th
Crisfield Heritage Festival and Ward Foundation Chesapeake Challenge Decoy Contest
Jazz on the Waterfront Fest
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