Tradition + 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 the Virginia 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. 

Across the Region

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.

14th Annual Holiday Studio & Vineyard Tour, November 25-26
Annual Thanksgiving self-guided tour
Ten studios, two galleries and a vineyard
10 am to 6 pm each day
Download a brochure and map at the link above

Santa Train, December 3
Wish Santa safe travels on his way to the North Pole
Departs Cape Charles at 9:00 a.m.
Stops at seven towns along the way
Arrives at last stop in Parksley at 5:00 p.m.

Cape Charles

Festive Fridays, November 25 to December 23
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

Grand Illumination, Golf Cart & Boat Parade, December 3
Holiday lights and luminaries in Central Park
Golf carts decked to the halls and paraded through town
Lighted Boat Parade.

Bed & Breakfast Cookie Trail, December 11
Walk from one B&B to another
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!
Hors D’oeuvres, Raw Bar, Buffet Dinner & Dessert Bar.
Champagne toast at midnight!


Greater Exmore Business Association Open House, December 10
Complimentary holiday refreshments
Special discounts and offers
Come, shop, then stay to watch the Annual Christmas Parade

Annual Exmore Christmas Parade, December 10
Floats, prizes, giveaways and more
Santa and the colorful, festive parade roll down Main Street at 6 PM


Details for all events listed below are here

Holiday Homes Tour, December 10
Six historic Onancock homes decorated for the holidays
A rare opportunity to tour these beautiful homes
Learn about the unique history and architectural significance

In Onancock, Santa arrives by boat

Annual Music Festival, December 10
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 10
Meet him at the Onancock town wharf
Girls and boys, bring your holiday wish list

Santa’s Mixed Bag – A Merry/Christmas Spectacular, December 9-11
Theater production at North Street Playhouse

Christmas Parade, December 11
An old-fashioned holiday celebration


Details for all events listed below are here

Downtown Tree Lighting Celebration, November 26
Chincoteague’s holiday season officially begins! Music and caroling.

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

“Savor the Season” Progressive Tour, December 1
A dozen homes decorated for the holidays

Chincoteague Homes for The Holidays Tour, December 3
All proceeds to benefit the Island’s Holiday Tree Lighting

Old-fashioned Christmas Parade, December 3
Floats, bands, fire companies, Santa

Santa Visits Island on Firetruck, December 20 & 21
Santa tours the island on a ladder truck making merry in the evening
North Chincoteague – Dec. 20th, South Chincoteague – Dec. 21st.
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 (2017)
Plunge into the icy Atlantic Ocean
Come in costume. Or not.

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