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October Festival Guide in Virginia’s River Realm

The fall is the best time of year to take a trip to Virginia’s River Realm. The reflection of the fall leaves on our rivers is breathtaking and inspiring. The fall is also the best time to enjoy local oysters. Wild harvested oysters spawn during the summer, when water temps are warmest. They’re the plumpest and most delicious during the fall. But you can eat oysters year ‘round  thanks to oyster farmers. These cage raised oysters are designed to spend all their time growing (and not spawning) so they are tasty every time of the year. You can enjoy them at these festivals along with wine, art, live music, and more.

We’ve broken down the highlights and where to stay during your festival weekend journey.

Farmers’ Markets

Irvington Commons, King Carter Driver, October 6

Kilmarnock Town Centre Park, 150 N. Main Street, October 27

These markets operate 9 am -1 pm and are just the place to grab a pumpkin to take home. These are family and dog friendly events to enjoy a River Realm fall.

Music on the Half Shell Stage

October 18, 5 pm-8:30 pm

Music on the Half Shell Stage: 7th Street Band

Kilmarnock Town Centre Park, 150 N. Main Street, Kilmarnock, VA

Grab a blanket or chair and your dancing shoes, it’s time to dance to Motown at the Park. The outdoor amphitheater features food and beverage vendors and is family friendly. No dogs or coolers however.

Cost: Tickets are only $5 per person.

Where to Stay: Make it a LONG weekend with some deluxe accommodations at the Kilmarnock Inn. Tucked in less than a block off of Main Street, this Presidential themed inn is a short walk to Town Centre Park. Try the amazing bloody Mary’s there for brunch!

Urbanna Wine and Oyster Stroll

October 13,  4 to 7 p.m.

Town Green, Urbanna, VA

Stroll the charming Town of Urbanna during this annual foodie event.  Shop and restaurant owners in the a historic port town open their doors to offer food and wine tastings.  Kick things off with oyster tastings at the Urbanna Town Green where live music will be playing all evening. Take on the town by foot and meet the friendly faces behind the businesses of Urbanna. Be sure to walk down to the Town Marina and see Urbanna Creek’s beautiful boats and water vistas.

Cost: $20.00, which includes tastings at participating shops and restaurants, commemorative wine glass, and oyster tastings at the Urbanna Town Green. Purchase tickets online or at Cyndy’s Bynn, Lowe Tide, Marshall’s Drug Store, If It’s Wood and More, Something Different, ReSail Boutique, Grounded, Big Oak Cafe’ and The Table at Wilton.

Where to Stay: You’ll want to be sure to stay close to the festival. Nearby accommodations include The Inn at Urbanna Creek, The Chesapeake Inn or Atherston Hall Bed & Breakfast.

Holly Point Art and Seafood Festival

October 20, 10 to 4 p.m.

Deltaville Maritime Museum,  287 Jackson Creek Rd, Deltaville, VA

This lovely Maritime Park, located on the banks of Mill Creek, is just minutes away from the Chesapeake Bay.  It provides a wonderful natural background to leisurely stroll through 60 vendors selling unique art creations and a car show.  There will be a variety of seafood, festival food and beverages with live music throughout the festival day.

Peruse the museum’s maritime exhibits, walk the nature trails with beautiful sculptures, tour antique boats displayed on the water, take a creek cruise, and enjoy the children’s garden complete with a train.  Bring your kayak or paddleboard and use the museum’s launch to explore the local marine life.  It’s a great way to spend the day with your family.

Ray Pittman and the Revival play 10:30 am-2 pm in the Pavilion.

Cost: Free

Where to Stay: Boat in and stay at one of the marinas in Deltaville, the Boating Capital of the Chesapeake, or how about Edentide, a B & B  or The Chesapeake Inn in walkable Urbanna.

Bay Seafood Festival


October 20, 4:30 – 10 p.m.

Camp Kekoka, 1083 Boys Camp Rd., Kilmarnock VA

This Signature Event is a fun, foodie friendly festival has been kicking fall off in Kilmarnock for 27 years. Hosted by the Kilmarnock, Irvington White Stone Rotary. The all-you-care-to-eat festival raises funds for a variety of nonprofits throughout the River Realm. The Bay Seafood Festival takes place on the banks of Indian Creek, just minutes from the Chesapeake Bay-you can boat in or drive in. Bring your dancing shoes.  En*novation will keep the party for a cause dance floor full! But get your tickets early. This event ALWAYS sells out and tickets are not sold at the door.

Cost: $50 per person, which includes all you can eat, soda and water. Adult beverages are also for sale.

Where to Stay: Get in touch with your presidential side at the Kilmarnock Inn. The quaint and enchanting bed and breakfast is a short drive from more than just the festival!

Oktoberfest Festival

October 27, 9 AM-3PM

White Stone Volunteer Fire Department Grounds, White Stone, VA

This one is for beer and brat lovers. Journey to the River Realm for this unique take on the well known Oktoberfest traditions of beer, food, dancing, and more. White Stone’s Oktoberfest Festival raises funds to support the White Stone Fire Department. Enjoy the fall festival featuring arts, crafts, a bake sale, face painting classic car show, chili cook off competition, live local bands and more.

Cost: Free to attend. Food, beverages, art and more for sale.

Where to Stay: 

Cozy up after a day of food, drinks, and fun at the Kilmarnock Inn or the Hope and Glory Inn. Both will offer a quaint, yet magical place to rest your head.

Find more great things to experience in Virginia’s River Realm in October and all year long!