Chincoteague’s 2016 Fall Festivals

Fall is a lovely time to visit Chincoteague Island.  The ocean is warm, the summer crowds are gone, and you’ll have most of the restaurants and shops to yourself. There’s plenty to do, too– we have a full schedule of events coming up this fall.  Here’s a sample of the fun activities and festivals going on during the next few months.


Sept 10, 2016- Plein Air Art Show.
Each year, the 2nd week of September brings more than 50 fine artists from the Mid-Atlantic and beyond to paint “en plein air” (French for painting outdoors) on Chincoteague and Assateague.  On Saturday evening, you can see what they’ve created at a Show and Sale that is free to the public.  Come early, as the best pieces sell quickly.  A portion of the artwork sold benefits CCA. 6pm-9pm at the United Methodist Church Social

Sept 10, 2016- Chincoteague Police Dept Poker Run for Kids.
Ride starts at Stingrays in Capeville, and is Police escorted to Chincoteague! This year, we will have two bands! The Route 13 Band will play before the auction in Robert Reed Park, and Front Page News Band will ROCK us for the Block Party! For more information call 757-336-3155 or click here.

Sept 24, 2016- Chili Chowder Cookoff.
Sponsored by the Chincoteague Volunteer Fire Company, the 17th Annual Chili Chowder Cook-off will be held at the Chincoteague Island Carnival Grounds from 11am-5pm. Free Admission. Live Music, Arts & Crafts Vendors, Great Food, Raffles, Family Fun. Little Miss Chili Pepper and Mr. Hot Stuff Competition and more. Call 757-894-8771 or visit for more information and event applications.

October 7&8, 2016- CVFC Fall Pony Roundup
On Friday afternoon (around 4:00pm-4:30pm), the cowboys will round up the southern end of the pony herd and corral them into the south pen on road going out to the beach on Assateague. This round up usually takes a couple of hours and there is plenty of parking access to the ponies for the crowd to see. Saturday morning (around 7:30am) the cowboys head up the service road to round up the northern end of pony herd and corral them into the north pen. This is area is not as easily accessible to the public because it requires a three mile walk up the service road and then wait for the ponies to come into the corral and then a three mile walk back.

October 8, 2016- Oyster Festival
Come enjoy a day full of oysters, oysters, oysters!  Oysters on the half shell, steamed, single fried & fritters, clam chowder, clam fritters, salad bar, Boardwalk fries, hush puppies, hot dogs, beverages & more!  Noon-4PM. Tom’s Cove Park – 8128 Beebe Road. $45 per person (ages 5 & up).  For more information visit the Chamber office, call 757-336-6161 or to purchase tickets online visit

Oct 22- Cork and Canvas Wine Festival.
Held just down the street at Maddox Campground, Cork & Canvas is a wine festival and art show that includes live music, great food, an artisan market and kids’ entertainment. This day-long festival offers samplings from a variety of Virginia wineries.