Traditional + Quirky: The Holidays on VA’s Eastern Shore

There are the traditional holiday home tours, lighting ceremonies and old-fashioned Christmas parades in small towns across Virginia’s Eastern Shore during the holidays. But there are other celebrations unique to the region.  In the harbor town of Onancock, Santa Claus arrives by boat, of course. In Chincoteague, Mrs. Claus holds a Christmas tea party. On New Year’s Eve, watch a crab pot or a horseshoe drop at the stroke of midnight. On New Year’s Day, revelers brave the icy Atlantic Ocean, costumes and all.

It’s the holidays like they used to be with a little quirky fun thrown in. Selected holiday events are listed below; for a complete list, go here. 


Virginia’s Eastern Shore Artisan Trail
Shop across the 70-mile Eastern Shore, along two coastlines
Over 50 artist and artisan studios, agri-artisans, gift stores, museums, gourmet grocers
Buy local arts and crafts, food, wine, seafood and more
Self-guided tour using detailed map
An excellent way to find one-of-a-kind holiday gifts

Pick up an Artisan Trail brochure wherever you see this sign.

Annual Holiday Studio & Vineyard Tour, November 24-25
Annual Thanksgiving self-guided tour
41 artists across 14 sites and one winery
10 a.m. to 5 p.m. each day
Download a brochure and map at the link above

Eastern Shore Madrigal Singers Annual Christmas Performance, December 1 &3
A mix of traditional and fun holiday songs
Performances in Franktown and Chincoteague

Santa Arrives By Truck, December 2
Wish Santa safe travels on his way to the North Pole
Departs Cape Charles at 9:00 a.m.
Stops at five towns
Arrives at last stop in Parksley at 3:00 p.m.


Festive Fridays, November 24 to December 22
All shops are open until 8:00 p.m.
Discounts, door prizes
Open houses
Carriage rides
Santa and Mrs. Claus
Special deals at local restaurants

Grand Illumination in downtown Cape Charles

Friendsgiving, November 22
Oysters shucked by local watermen
Live music

Grand Illumination & Golf Cart Parade, December 2
Holiday lights and luminaries in Central Park
Golf carts decked to the halls and paraded through town

Lighted Boat Parade, December 9
Boats decked out for the holidays sail around the town harbor

A Beggar’s Christmas, December 9 & 10
Theater production at the Historic Palace Theater

Bed & Breakfast Cookie Trail, December 10
Tour B&Bs and private homes
Enjoy holiday cheer at each stop

Annual Dropping of the Crab Pot, December 31
A local New Year’s Eve tradition
Honors the waterman/fishing culture

New Year’s Eve at the Oyster Farm, December 31
Party til the ball drops with live music


Twisted Chimney Christmas Workshop and Book Reading, December 3
Book reading of a local holiday favorite
Ornament making


Brownsville Holiday Open House, December 14
Tour historic Brownsville
Enjoy wagon rides, a bon fire and treats


Holiday Open House, December 9
Treats and special offers from 10 a.m. to 5 p.m.

Annual Exmore Christmas Parade, December 9
Floats, prizes, giveaways and more
Santa and a colorful parade roll down Main Street at 6 p.m.


Grand Illumination, December 2
Tree lighting and bonfire on the waterfront


The Nutcracker, December 15-17
Live performance of a Christmas classic
Call (757) 442-3226 for tickets


Sixth Annual Holiday Market, November 18
Vendors selling seasonal produce, art, gifts and decorations

White Christmas, December 7
Free screening of this Christmas classic

Holiday Homes Tour, December 9
Six historic homes decorated for the holidays
A rare opportunity to tour these beautiful homes
Learn about the unique history and architectural significance


Santa arrives by boat in the harbor town of  Onancock. Photo credit:


Annual Music Festival, December 9
Free and open to the public
Held at the Historic Cokesbury Church
Variety of musical performances
Christmas carol sing-along

Santa Arrives by Boat, December 9
Meet him at the Onancock town wharf
Girls and boys, bring your holiday wish list

The Best Christmas Pageant Ever: The Musical, December 8 & 9
Theater production at North Street Playhouse

Holiday Open House at Ker Place, December 9
See a Federal-era manor house decorated for the holidays

Local Artist Open House at The Historic Onancock School, December 9
Shop for local and handmade Christmas gifts crafted by local artisans

Christmas Parade, December 10
An old-fashioned holiday celebration


Old Fashioned Christmas, December 3
Small town Christmas
Christmas music, refreshments and a tree lighting


Details for all events listed below are here

Holly Day Market and Wildlife Art Gallery, November 25
Shop arts, crafts, jewelry and holiday decor from over 80 vendors.

Downtown Tree Lighting Celebration, November 25
Chincoteague’s holiday season officially begins! Music and caroling.

How about an icy New Year’s Day plunge into the Atlantic?

Chincoteague Homes for The Holidays Tour, December 2
Get a peek inside beautifully decorated homes.

Old-fashioned Christmas Parade, December 2
Floats, bands, fire companies, Santa

“Savor the Season” Progressive Tour, December 8
Visit three beautifully decorated homes and enjoy a three-course meal along the way.

Children’s Tea Party with Mrs. Claus, December 10
Share sweets, songs, gifts and games with Mrs. Claus.


Xmas by the sea
Chincoteague Island celebrates Christmas in a big way.


Santa Visits Island on Firetruck, December 19 & 20
Santa tours the island on a ladder truck making merry in the evening
North Chincoteague – Dec. 19th, South Chincoteague – Dec. 20th.
When you hear the siren coming, go out and say hello!

Pony Island Horseshoe Drop & Costume Promenade, December 31
Wild costumes, prizes awarded
Lighted horseshoe drop at midnight

New Year’s Day Polar Pony Plunge, January 1 (2018)
Plunge into the icy Atlantic Ocean
Come in costume, or not

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