Main Street Merchants Events for 2020


We are coming together, virtually of course, to make Shop the Dock the best online LOCAL shopping experience for you until we are back up and running in person. 

As we head into the Shop The Dock virtual market, we would love to inform you of the changes we have made. We will be hosting our virtual market in the Facebook group here. This will make our page run seamlessly while you are shopping and we are featuring vendors. Head on over to see what we have been working on and follow the page to be ready to shop!

You'll be able to shop multiple local vendors for terrific deals! Contact Anne Clark at or (757)336-5715.

Giant "LOVE" Adirondack Chairs Robert Reed Waterfront Park 

LOVEWORKS! Come downtown and sit in seats fit for giants! Four large Adirondack chairs in our beautiful waterfront park bordering historic downtown! Each chair holding a letter to spell "LOVE" located on the happiest seaside island in Virginia... the state that is for LOVERS!​

International Migratory Bird Day Youth Art Contest Sponsored by the Main Street Merchants 

Calling all young, aspiring wildlife artists! The staff from Chincoteague National Wildlife Refuge invites you to enter your work in an art contest that will be held as part of the International Migratory Bird Day celebration that is held at Wildlife Refuge.

Trick or Treat Main Street!  Sponsored by the Historic Main Street Merchants 

Dress up for Halloween and come trick or treat at participating Main Street Merchant locations up and down Chincoteague's Main Street and in Robert Reed Park (Thursday, October 31) from 4:00 to 7:00pm... Locations that are participating will have an orange & black "Trick or Treat on Main Street" sign on their doors. This year we've expanded the event into Robert Reed Waterfront Park to allow more room for local merchants: businesses will have tables set up there to hand out candy! There will also be a Window Decorating Contest for the Main Street Merchants... (Stay tuned for the list of participating merchants as the event approaches) Please contact Tabitha Borum for more info at 757-790-9907.

The Chincoteague Homes for the Holidays Tour

"Every house on Chincoteague has a unique story to tell." The Homes for the Holidays Tour is held on the same day as the charming old fashioned Christmas parade, so mark your calendars and start planning for a fun-filled holiday weekend!  All proceeds from the ticket sales go to the Manna Cafe, a local organization that provides free hot lunches every Monday from 11-1 at the Christ Methodist Church on Chincoteague. Manna Cafe also provides meal delivery to people who are homebound. Please contact Kim Dennis at 703-599-4430. Click here for the Facebook page with LOTS of great, up to the minute info!

​Annual Chincoteague Old-fashioned Christmas Parade
Fill the sidewalks on Main Street from Maddox Boulevard to the Chincoteague Volunteer Fire Company Fire House to see enchanting floats, bands, marching units, decorated boats, fire companies from across the Eastern Shore, equestrian teams, classic cars, and more. Keep an eye out for Santa too! After the parade's conclusion, the festivities continue at the Chincoteague Firehouse. Visit with Santa while enjoying refreshments served by the Kiwanis Club of Chincoteague. Cheer for parade participants when trophies are awarded by the Chincoteague Chamber of Commerce!

SHOP THE DOCK'S Christmas Craft Show at Don's Seafood Restaurant

Monday, December 21, 2020 from noon to 4:00pm

Children's crafts, vendors, a giveaway for customers, food, and drinks will all be available! Admission is completely free so bring your whole family! Contact Anne Clark at or (757)336-5715. Check the event page here.

New Year's Eve Horseshoe Drop and Costume Promenade
The end of year celebration that culminates in a promenade of crazy costumes just before the countdown to midnight -- then the lighted horseshoe drops just in time to ring in the new year. To become totally immersed in the oddest of silly visual spectacles, head for the Robert Reed Downtown Waterfront Park around 10:30pm...  Bring your camera to capture the spectacle, dress warmly, wear a hat and gloves for sure, and comfortable shoes so you can dance, but most importantly -- bring family and friends with you to enjoy the fun that is all Chincoteague! Sponsored by Christmas by the Sea. 

New Year's Polar Plunge at Assateague Beach

Presented by Christmas by the Sea
Nothing can compare to the invigorating feeling you get by plunging into the ice-cold waters of the Atlantic Ocean on January 1st! It really is an awesome experience. There will be lots of fun all around. Plungers are encouraged to dress up in the zaniest, craziest costume they can imagine! Visit for more info or download the plunge waiver here. 

Death By Chocolate

Created and sponsored by the Historic Main Street Merchants  


Our famous Valentine's weekend scavenger hunt! Complete your playing card while enjoying delicious chocolate treats at each participating merchant. Cross the finish line at the Chincoteague Center to have your playing card validated and entered in the grand prize drawings. We have over 35 prizes and you must be present  to win. Playing cards can be picked up from any participating merchant during the event. You must be 18 or older to be entered in the grand prize drawing. Visit us on Facebook for a complete list of participating merchants! Grab that someone special or some friends and make a weekend of it! Come and experience  all the beauty of Chincoteague Island! Please contact Nicole at 443-614-6801 for more information.


Annual Volunteer Firemens Carnival
Rides, food, fun! Carnival to help celebrate the world famous pony swim and auction. 

Annual Charity Poker Run / Block Party
Downtown fun! Sponsored by Chincoteague Police Department all proceeds benefit a childrens' charity.

Chili Chowder Cookoff and Car Show
Annual fall festival at the Chincoteague carnival grounds with food, entertainment, classic cars and more: sponsored by the Chincoteague Volunteer Fire Company. Hope to see you for all the food and festivities! Email for more info.

Chincoteague Island Farmers' Market
6309 Church St. CCA Headquarters
Wednesdays and Saturdays during the season from 9:00am - 1:00pm
Fresh produce, seafood, plants, flowers, handmade crafts, and more! 

To participate, call (757)894-2512.

2nd Saturday Art Strolls
April through November participating galleries and shops have art demonstrations, music, readings, craft making, and more... For more info call the Chincoteague Cultural Alliance at (757)336-0044 or visit their website here.

Music @ the Dock * Robert Reed Waterfront Park
Sponsored by Chincoteague Cultural Alliance. A series of public concerts performed each summer in Robert Reed Park along the Waterfront in Downtown Chincoteague. The concerts are FREE and each presents a different style of music. Bring a chair or blanket and sit on the lawn or listen from your boat docked on the waterfront.

Chincoteague Island Arts Organization (CIAO) and The Island Theatre and Annex
4074 Main Street, downtown Chincoteague Island   ​phone 757-702-2170
CIAO was incorporated in Virginia as a non-profit cultural arts center on Chincoteague Island to share film, performing arts, education programs, and other entertainment with the island community and its visitors. They host events such as concerts, plays,  performances, game days, classic film showings and more! Check their Facebook page and their website for more info!