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Cape Charles Fall and Winter Event Guide



Cape Charles is wonderful all times of the year, especially in the fall! This year’s fall event guide can help you decide everything from the best dates for your trip to all the fun happenings and activities you can look forward to when you stay with us here at Cape Charles Yacht Center!


Book your slip and stay with us at our new studio apartment on-site! You can view our Captains Quarters here.


Cape Charles Fall Event Guide

Halloween Weekends at Chesapeake KOA Resort

Celebrate the coming spooky season with Cape Charles / Chesapeake KOA Resort’s Halloween Weekends! Held every weekend for the entire month of October, this event will feature all your favorite Halloween activities and more, such as trick or treating, costume contests, all the sweets and food you can eat, games, prizes, and a monster mash party to wrap it all up.


Come in your best Halloween costume and get ready for a night full of spooktacular fun every weekend in October at the Cape Charles / Chesapeake Bay KOA campground.


St. Charles Oktoberfest

Welcome the month of October with the St. Charles Oktoberfest, a family-friendly Oktoberfest celebration being held right here in Cape Charles. This event will feature everything you love about Oktoberfest, like craft brews, fine wines, good food, live music, craft vendors, fun games, and even a silent auction. Best of all, this is all to benefit the historic 137-year-old St. Charles Church.


Feel like a part of this tight knit community and have some great fun while you’re at it! St. Charles Oktoberfest takes place on October 8, 2023, from 12 PM to 5 PM at the St. Charles Catholic Church in Cape Charles.


Vets & Pets

The famous canine watersports event is back for another year at Cape Charles on Veterans’ Day weekend! Vets & Pets Dock Dogs Classic is the premier canine aquatic sports event in Cape Charles, featuring cute pups competing in numerous sporting events. Plus, veterans and their pets get special discounts for lodging, restaurants, and select local shops during this event!


If you’re a dog lover, this is an event you won’t want to miss. Vets & Pets takes place from November 11 to 12, 2023, in Cape Charles.





Holiday Market

Start off the holiday season right with Chesapeake Bay KOA’S annual Holiday Market. Bringing together plenty of local vendors selling unique handmade crafts and wares, you’re sure to find the perfect gift for all your friends, family, and loved ones,and maybe even something for yourself! This event also features food vendors with special holiday treats.

Begin your holiday shopping early on November 18, 2023, at Chesapeake Bay KOA.


Festive Fridays

Every Friday starting November 24, 2023, stroll through a quaint winter wonderland at Festive Fridays, only here at Cape Charles. Do some special Christmas shopping, listen to carolers and other musical performances, take photos with Santa Claus and Mrs. Claus, take carriage rides through the streets, watch classic Christmas movies at the Historic Palace Theatre, and savor the holidays right here in Cape Charles!


Festive Fridays are free for everyone to attend at happens every Friday from November 24 to December 29, 2023, from 5 to 8 PM at Cape Charles Main Street.





Cape Charles Museum Oyster Roast Fundraiser

The Cape Charles Museum and Cape Charles Historical Society proudly present their annual Oyster Roast Fundraiser event! This event features live music from Ghost Town Union, a live auction, and a veritable feast of roasted oysters and other favorites like fried chicken, chowder, potato salad, desserts, beer, and wine.


Support a good cause and have a great time with friends and family at the Oyster Roast Fundraiser on November 25, 20234, at the Cape Charles Museum from 4 to 8 PM.


Historic Cape Charles Cookie Trail

Have a unique, holiday-themed walking tour of the Cape Charles Historic District with this year’s Historic Cape Charles Cookie Trail! Visit participating homes and B&B’s for a glimpse into their historic architecture, beautiful Christmas decorations, and a delicious seasonal treat. You can visit as many homes as you want, or visit them all, and go in any order until you’re done. Some places may even offer some special food and drink items for anyone going on the tour, along with special Christmas ornaments and other items for sale.


The only price of admission is a donation of a non-perishable food item to the Eastern Shore Food Pantry and Food Bank. After that, just register and pick up your map at the Almeta Café in the Hotel Cape Charles, and you’re good to go! The Historic Cape Charles Cookie Trail happens on December 9, 2023, from 2 to 5 PM.


As the weather grows colder and we near the end of the year, Cape Charles will always be here to welcome you, all year round! Book a slip with us at Cape Charles Yacht Center and be sure to attend any or all of the above fall and winter events.




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