Urbanna Family Friendly Events

The Annual 2026 Dan Gill's Bodacious Chili Cook-Off is FREE to everyone!

All chili chefs are invited to enter the Chili Cook-Off contest.

This year we will award our biggest prize ever to the winner!

All chili chefs are invited to enter the Chili Cook-Off contest for a chance to winn $500 by popular vote!

Visitors to the cook-off can sample the variety of chili available and vote for their favorite. Prizes, along with bragging rights, will be awarded for 1st ($500), 2nd ($250), and 3rd ($75) place.

We encourage all contestants to get creative and “dress up” their booths to add even more fun to the festivities. A winner will be chosen.

The cook-off is being held at 213 Virginia Street in Something Different’s parking lot with a beer garden and music. Enjoy your favorite beverage while tasting some of the best chili in the region. It’s February, so this event is rain or shine, cold or hot. If it’s cold, burn barrels will be strategically located to keep you warm!

Click the link below for complete details and to register.

Kiwanis of Middlesex Proudly Present
Mardi Gras

Live Music by En Novation
Food, drinks, music, wine pull, raffles, auctions, and fun galore
Bethpage Camp Resort

CLICK HERE to learn more.

Stock up on homegrown and homemade treats, flowers and plants, just-picked produce, fresh-baked goods, all natural homemade pet treats, artisan cheeses, clothing, jewelry, soaps, candles, local honey, and who knows what else. Visit our special section just for local artists!
9am to 1pm

CLICK HERE to learn more about Participation or Sponsorship

The pool will not be open for this event.

Come on out and bring the whole family for music, delicious food, great vendors, and so much more! Plus, the Urbanna pool will be open for some fun in the sun! Just pay at the swimming pool gate to dive in. Remember, IDs will be checked at the entrance tent, so don’t forget yours!

Musical Entertainment: MIchael Clark Band

4 to 8pm ~ Taber Park

On the grounds of a stately 17th century plantation, Arts in the Middle offers two days of entertainment in Virginia's River Realm with fine arts and fine crafts, music and local foods a stroll away from Urbanna, the area's most charming waterfront village.

ArtsInTheMiddle.com

Stock up on homegrown and homemade treats, flowers and plants, just-picked produce, fresh-baked goods, all natural homemade pet treats, artisan cheeses, clothing, jewelry, soaps, candles, local honey, and who knows what else. Visit our special section just for local artists!
9am to 1pm

CLICK HERE to learn more about Participation or Sponsorship

Come on out and bring the whole family for music, delicious food, great vendors, and so much more! Plus, the Urbanna pool will be open for some fun in the sun! Just pay at the swimming pool gate to dive in. Remember, IDs will be checked at the entrance tent, so don’t forget yours!

4 to 8pm ~ Taber Park

Come to Urbanna for a Town-Wide Yard Sale. You're sure to find something you love. Urbanna businesses and residents will particpate. There will be a Google map available with the loaction of each yard sale.

8am to 2pm

Stock up on home grown and homemade treats, flowers and plants, just-picked produce, local pasture raised beef, fresh baked goods, artisan cheeses, clothing, jewelry, soaps, candles, local honey and who knows what else. Visit our special section just for local artist!
9am to 1pm

CLICK HERE to learn more about Participation or Sponsorship

Come on out and bring the whole family for music, delicious food, great vendors, and so much more! Plus, the Urbanna pool will be open for some fun in the sun! Just pay at the swimming pool gate to dive in. Remember, IDs will be checked at the entrance tent, so don’t forget yours!

4 to 8pm ~ Taber Park

Founders Day: A Celebration of Urbanna's Colonial History

Save the Date
Founders Day is Coming!

Stock up on home grown and homemade treats, flowers and plants, just-picked produce, local pasture raised beef, fresh baked goods, artisan cheeses, clothing, jewelry, soaps, candles, local honey and who knows what else. Visit our special section just for local artist!
9am to 1pm

CLICK HERE to learn more about Participation or Sponsorship

Come on out and bring the whole family for music, delicious food, great vendors, and so much more! Plus, the Urbanna pool will be open for some fun in the sun! Just pay at the swimming pool gate to dive in. Remember, IDs will be checked at the entrance tent, so don’t forget yours!

4 to 8pm ~ Taber Park

Stock up on home grown and homemade treats, flowers and plants, just-picked produce, local pasture raised beef, fresh baked goods, artisan cheeses, clothing, jewelry, soaps, candles, local honey and who knows what else. Visit our special section just for local artist!
9am to 1pm

CLICK HERE to learn more about Participation or Sponsorship

Come on out and bring the whole family for music, delicious food, great vendors, and so much more! Plus, the Urbanna pool will be open for some fun in the sun! Just pay at the swimming pool gate to dive in. Remember, IDs will be checked at the entrance tent, so don’t forget yours!

4 to 8pm ~ Taber Park

From 2 to 5pm Stroll along the charming streets of Urbanna while tasting samples of wine and oysters. Live music!

Come to Urbanna for a Town-Wide Yard Sale. You're sure to find something you love. Urbanna businesses and residents will particpate. There will be a Goole map available with the loaction of each yard sale.

8am to 2pm

Cut-off for registration is Thursday, October 16, 12pm.

Put on your spookiest or funniest costume and hit the streets like you’ve never done before. Halloween is the perfect time to celebrate it here with wicked music, ghoulish friends, and spooktacular beverages. Crawl to our favorite haunts in Urbanna!

Urbanna Oyster Festival

Virginia’s official oyster festival. Highlights include Friday night’s Firemen’s Parade (7pm), Saturday’s Virginia State Oyster Shucking Contest (11am) and the right-out-of-Norman-Rockwell Oyster FestivalParade (2pm).

Friday: 9am to Midnight

Saturday: 9am to 6pm

Holiday Fashion Show & Luncheon

Notice: We are having the fashion show today.

Enjoy lunch while local models show you the latest fashions from Urbanna's boutiques.

11:30am at The Chesapeake Inn, 250 Virginia Street. Tickets $35.

Purchase tickets online below or ReSail Boutique.

Annual Lighting of the Trees

Join us for the annual festival of trees at 4:30pm December 6th at historic Lansdowne, 271 Virginia Street.

If you are interested in being a sponsor of this year’s event please contact Sandra Rudy – 804-837-1108

The famous Urbanna Christmas parade is now an all-day family event. It begins with “Breakfast with the Elves” and finishes with the spectacular Christmas parade. In between you’ll find alpacas, Christmas crafts for kids, wine tastings, a pet parade and more!

Click here for full schedule and offerings.

Want to enter a float or participate in the parade?
Click here

Explore five uniquely decorated homes and enjoy open houses at The Urbanna Scottish Factor Store & Museum and Landsdowne.

Homes to be announced soon. Follow us on Social Media!

Details will be provided November 2026

Please do not call Urbanna Town Hall with questions. This is an Urbanna Business Association event.
Contact: uba@urbanna.com

Please use the link at the top of this page to join our email list to stay informed about the Polar Express tickets.

Climb into your toastiest PJs, grab your Golden Ticket, and come aboard the Urbanna Polar Express.

Get ready for a journey to the North Pole with magical stops full of surprises and to meet your favorite characters along the way. Santa and Mrs. Claus will be waiting at the North Pole for all Believers!

The Polar Express will run two magical nights with six runs each night.

Note: Preorder tickets are not available.

December 12 and 13
Boarding Times
Trolley No. 1: 5:00pm ~ 6:30pm ~ 8:00pm