Events

In Cape Charles, it’s easy to find a cause to celebrate — and not just in the summer months. Mark your calendar for these fun-filled upcoming events.

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Live Local-ISH Festive Friday Pop Up!

Live Local-ISH is located at 22 Strawberry Street in Cape Charles. Inspiring Shore Hospitality, and dedicated to supporting artisans of the Eastern Shore, Live Local-ISH will host pop up events during Festive Friday’s and offer creations from Eastern Shore Painted Furniture, JK Pottery, Shooting Star Gallery, Eastern Shore Arts and others! Stop by and meet […]

Free
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Festive Fridays

You're invited to Festive Fridays in Cape Charles! Friday evenings from Thanksgiving through Christmas, experience Cape Charles' holiday charm & enjoy many FREE Friday night festivities for the whole family. Each Friday will feature community entertainers, shops open until 8 p.m., restaurant specials, family holiday movies and activities along Mason Avenue and Strawberry Street.

Historic Home Cookie Trail

December 11, 2:00-5:00 pm, Historic Home Cookie Trail, hosted by the Vacation Homeowners of Cape Charles, 309 Jefferson Ave. Free with a donation to the Cape Charles Food Bank. Drop off donations, pick up event map and indulge in holiday shopping with local vendors at Cake Charles, 309 Jefferson Ave.

Free

Tool Mania

Cape Charles Volunteer Fire Company 501 Mason Ave, Cape Charles, VA

Cape Charles Volunteer Fire Company will host it's 15th annual tool mania this year! Always a favorite holiday event and a great cause to raise money for our local Fire Department. There will be raffles, silent auctions and door prizes. For Tickets Call: (757)651-5154 or (757)635-2003  

First Annual Holiday Sip & Shop

American Legion Post 56 21210 N. Bayside Rd., Cheriton, VA

The holidays are just around the corner! Don't wait until the last minute - come and find your perfect gifts while enjoying a fun and relaxed holiday shopping experience with several local artists and vendors. Food and beverages will be available for purchase and there will be 50/50 raffle all are welcome to participate in. […]

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Popup Holiday Shop

Mason Avenue Mason Ave, Cape Charles, VA

Focus Optical Boutique will be hosting a pop up holiday shop in the store at 232 Mason Avenue each Festive Friday. Unique holiday gifts will be available, ALL of the items are MADE IN AMERICA, supporting small businesses from across the country. Not just optical items, there is sure to be something for everyone on […]

Recurring

Live Local-ISH Festive Friday Pop Up!

Live Local-ISH is located at 22 Strawberry Street in Cape Charles. Inspiring Shore Hospitality, and dedicated to supporting artisans of the Eastern Shore, Live Local-ISH will host pop up events during Festive Friday’s and offer creations from Eastern Shore Painted Furniture, JK Pottery, Shooting Star Gallery, Eastern Shore Arts and others! Stop by and meet […]

Free
Recurring

Festive Fridays

You're invited to Festive Fridays in Cape Charles! Friday evenings from Thanksgiving through Christmas, experience Cape Charles' holiday charm & enjoy many FREE Friday night festivities for the whole family. Each Friday will feature community entertainers, shops open until 8 p.m., restaurant specials, family holiday movies and activities along Mason Avenue and Strawberry Street.

Virginia Symphony Holiday Brass

Historic Palace Theatre 305 Mason Ave., Cape Charles, VA

The bold sounds of the Virginia Symphony brass section ring in the holidays with a blast! Experience the festive sounds of the season in a concert filled with wit, virtuosity, and the glorious music of the holidays—featuring the VSO brass and percussion sections in an all-new program. You’ll enjoy music from a variety of styles […]

$25

Community Sing

Historic Palace Theatre 305 Mason Ave., Cape Charles, VA

Join neighbors and friends in the Historic Palace Theatre to sing Christmas Carols accompanied by a pianist on the Steinway. Adulta and children welcome!

Free

New Year’s Eve Crab Pot Drop

Central Park Monroe & Plum St, Cape Charles VA, VA

Watch the crab pot drop at 10 p.m. on Mason Avenue. Why 10 p.m? It is midnight in Greenland. This allows family to be a part of the festivities without being out until midnight. Live entertainment starts at 9 p.m.

Free

First Day in the Bay Polar Plunge

Madison Ave Beach Access

January 1, 11:00 am, Third Annual First Day in the Bay Polar Plunge, hosted by the Vacation Homeowners of Cape Charles, Madison Ave Beach Access. Ring in the New Year in the Bay! Come early, as the polar bears don't stay in the ocean for long!