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 23-24
Annual Thanksgiving self-guided tour
43 artists across 15 sites and one winery
10 a.m. to 5 p.m. each day
Download a brochure and map at the link above



Festive Fridays, November 23 to December 21
All shops are open until 8:00 p.m.
Discounts, door prizes
Open houses
Free movies
Carriage rides
Santa and Mrs. Claus
Special deals at local restaurants

Grand Illumination in downtown Cape Charles

Friendsgiving, November 21
Oysters shucked by local watermen
Live music

Lighted Boat Parade, December 1 
Boats decked out for the holidays sail around the town harbor

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

Candlelight Children’s Christmas Stories, December 7
Candlelight children’s Christmas story time
Complimentary refreshments.

Elf, Jr. The Musical, December 8, 9 & 15
Theater production at the Historic Palace Theater

Bed & Breakfast Cookie Trail, December 16
Tour B&Bs and private homes
Enjoy holiday cheer at each stop

Breakfast with Santa, December 16
Buffet breakfast and photo op. with Santa

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


Twisted Chimney Christmas Workshop and Book Reading, December 2
Book reading of a local holiday favorite
Ornament making


Brownsville Holiday Open House, December 6
Tour historic Brownsville
Enjoy wagon rides, a bon fire and treats


Annual Exmore Christmas Parade, December 8
Floats, prizes, giveaways and more
Santa and a colorful parade roll down Main Street at 6 p.m.


Grand Illumination, December 1
Tree lighting and bonfire on the waterfront


The Nutcracker, December 14-16
Live performance of a Christmas classic
Call (757) 442-3226 for tickets


Miracle on 34th Street, December 6
Free screening of this Christmas classic

Elf, Jr.: the MusicalDecember 7 & 8
Theater production at North Street Playhouse

Holiday Homes Tour, December 8
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 8
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 8
Meet him at the Onancock town wharf
Girls and boys, bring your holiday wish list

Holiday Open House at Ker Place, December 8
See a Federal-era manor house decorated for the holidays

Local Artist Open House at The Historic Onancock School, December 8
Shop for local and handmade Christmas gifts crafted by local artisans

Christmas Parade, December 9
An old-fashioned holiday celebration


Old Fashioned Christmas, December 2
Small town Christmas
Christmas music, refreshments and a tree lighting


Snacks with Santa and Crab Pot Christmas Lighting, December 2
Visit with Santa, then see a tree lighting like never before


Details for all events listed below are here

Holly Day Market and Wildlife Art Gallery, November 24
Shop arts, crafts, jewelry and holiday decor from over 80 vendors.

Downtown Tree Lighting Celebration, November 24
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 1
Get a peek inside 15 beautifully decorated homes.

Old-fashioned Christmas Parade, December 1
Floats, bands, fire companies, Santa

Children’s Tea Party with Mrs. Claus, December 9
Share sweets, songs, gifts and games with Mrs. Claus.

Savor the Season” Progressive Tour, December 15
Visit 4 beautifully decorated homes and enjoy a four-course meal and wine pairings along the way.


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


Santa Visits Island on Firetruck, December 12 & 13
Santa tours the island on a ladder truck making merry in the evening
North Chincoteague – Dec. 12th, South Chincoteague – Dec. 13th.
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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