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Dog Events in Cape Charles, VA

Here are the pet friendly events closest to Cape Charles. Use the links below to get details on each event, print directions, look at pictures, and even read reviews of last year’s event.

Pet Friendly Christmas Pawty in July at Big Ugly Brewing

Jul 11

Christmas Pawty in July at Big Ugly Brewing

Christmas Pawty in July at Big Ugly Brewing

Snap adorable pics with Beach Santa by When Skies Are Grey Photography by Denise, browse local vendors, and let your pup enjoy fun games and activities. Highlights include a pet costume contest, a dog ice cream eating competition, and plenty of cold brews for the humans.

Pet Friendly Annual Outer Banks Wright Kite Festival

Jul 17–18

Annual Outer Banks Wright Kite Festival

Kill Devil Hills, NC

Annual Outer Banks Wright Kite Festival

Take flight where flight first began! Enjoy a walk on the hallowed grounds where Wilbur and Orville took their historic first flight in 1903, then join the fun for some fun flight of your own. Large 30–100-foot kites will be flying high on display. Guests are welcome to fly kites of their own and take free stunt and power kite flying lessons.

Jul 24–25

Moby Watersports Festival at Whalebone

Moby Watersports Festival at Whalebone

Spend the day exploring Whalebone Junction during this fun, shop-local event featuring a scavenger hunt through participating businesses in the Whalebone shopping center. Pick up a scavenger hunt pamphlet, visit the shops, and return it to Kitty Hawk Kites to be entered for a chance to win a raffle prize. Along the way, enjoy food, drinks, and outdoor activities while taking in the scenic charm of the bypass. Not all shops are dog friendly so be sure to ask first before entering with Fido!

Aug 1

Run for the Paws 5K & 1M Dog Walk

Dewey Beach, DE

Run for the Paws 5K & 1M Dog Walk

A charity race and fun dog walk that raises funds for Humane Animal Partners while bringing the community and their pets together for a morning run/walk. The event includes a timed 5K, a 5K walk division, and a 1-mile dog walk.

Aug 6

Outer Banks Watermelon Festival

Outer Banks Watermelon Festival

Bring your furry friend to have fun at this event featuring a t-shirt tie dye station, watermelon-themed competitions, arts and crafts, face painting, food trucks and more! The event is free for guests to attend; however, the purchase of tickets is required to play and eat. Compete in classic competitions to win something from a selection of fantastic prizes.

Aug 8

Spoil Your Dog Day at James River Cellars Winery

Spoil Your Dog Day at James River Cellars Winery

Celebrate National Spoil Your Dog Day at James River Cellars with a fun-filled afternoon perfect for pups and their people! Enjoy live music, local food trucks, artisan vendors, and adoptable dogs available throughout the afternoon.

Select dates May 1–Aug 25

Wag Your Tail Tuesdays

Wag Your Tail Tuesdays

Bring Fido to the Bark in the Park, where he can enjoy the day for free with a donation to a local animal shelter. Acceptable donations include paper towels, treats, food and toys. This special event takes place at home on Tuesdays on the following dates: May 26, June 16, June 30, July 7, July 28 and August 11. There's also a Friday event on May 1 that welcomes pups.

May 21–Aug 27

Sounds of Summer Concert Series at Riverwalk Landing

Sounds of Summer Concert Series at Riverwalk Landing

Every Thursday there will be live music for you and your pup to enjoy. Guests are encouraged to bring blankets, chairs and small coolers. Please, no umbrellas, tables or tents. If you want something to munch on during the show, order dinner or dessert at any of Historic Yorktown’s waterfront restaurants.

Aug 29

Pints & Paws 5K and 1 Mile Run Walk and Pup Strut

Williamsburg, VA

Pints & Paws 5K and 1 Mile Run Walk and Pup Strut

A dog-friendly 5K, competitive walk, and 1-mile Pup Strut where leashed dogs may participate alongside their people. Hosted by 4 Paws Animal Rescue, Inc., the event also features a pup photo contest, vendors, and finish-line fun for a great cause.

Select games Mar 29–Sep 6

Bark in the Park with Norfolk Tides

Bark in the Park with Norfolk Tides

Take Fido out to a baseball game! Dog-friendly games are held on select dates throughout the season, so make sure to check the website's schedule to catch a game. Proceeds from dog tickets are donated to a local dog charity. Dog-friendly sections are 215-223 (3rd base side next to the Picnic/3B entrance). All dogs must enter the ballpark through the 1st Base Entrance and remain on a leash while at Harbor Park.

May 26–Sep 6

Paws & Pavement Club - Benefiting Worcester County Humane Society

Paws & Pavement Club - Benefiting Worcester County Humane Society

This weekly dog-friendly walk brings together pet lovers and their pups for a fun, social way to stay active while supporting local animal welfare efforts. Participants can walk, jog, or stroll at their own pace along a mapped route before enjoying food, drinks, tastings, and community time afterward. Registration includes event perks like giveaways and themed merchandise, with a portion of proceeds and donations benefiting the Worcester County Humane Society.

Jun 3–Sep 9, select

Bark in the Park - Best in Show Dog Days/Nights with the Richmond Flying Squirrels

Bark in the Park - Best in Show Dog Days/Nights with the Richmond Flying Squirrels

Bring your furry best friend to the ballpark every Wednesday home game throughout the season! Each week a different group will be celebrated. Dog sections can be found in sections 117 &118. Gates open at 5:30 PM.

Sep 11–12

Outer Banks Kite Festival

Outer Banks Kite Festival

Furry friends may join their owners to watch massive show kites flying high above the dunes at the park and participate in stunt and power kite lessons given by pros. Visitors will watch some of the nation’s most talented performers put on world-class displays of artistry and skill with kite flying set to music, synchronized shows and more.

Sep 19–20

Colonial Market & Fair at George Washington's Mount Vernon

Mount Vernon, VA

Colonial Market & Fair at George Washington's Mount Vernon

Step back in time at a lively, family-friendly marketplace inspired by the 18th century. Guests can browse handcrafted goods from skilled artisans, watch live demonstrations of traditional trades, and enjoy period-style music, food, and entertainment. Leashed dogs are permitted on the property with the exception of the following areas: the Mansion and all other historic buildings, the Ford Orientation Center, Donald W. Reynolds Museum and Education Center, the Shops of Mount Vernon, the Food Court and Pavilion, the Mount Vernon Inn Restaurant, and the Distillery & Gristmill.

Select May–Sep

Fridays at the Pavilion

Fridays at the Pavilion

Dogs are invited to join you in kicking off your summer weekends at this weekly event! Enjoy a toe-tapping, tail-wagging good time with live music from local bands, delicious bites from a rotating lineup of food trucks, and fresh wine options. Pets must be leashed but are welcome anywhere outdoors and the first floor of the winery. Bring a lawn chair or picnic blanket and spread out on the lawn.

Sep 25–26

Dewey's Golden Jubilee - Fall

Rehoboth Beach, DE

Dewey's Golden Jubilee - Fall

This beloved weekend celebration brings together Golden Retriever owners and pups for fun, beach time, and community spirit on both sand and surf. The event features informal gatherings like a Friday “Gold Rush” walk through nearby Rehoboth Beach, an unofficial beach romp, bonfires, and plenty of opportunities for dogs to play, swim and socialize. The relaxed festival atmosphere also supports the Morris Animal Foundation’s Golden Retriever Lifetime Study, one of the most comprehensive canine health research efforts in the U.S., and draws hundreds of Goldens and their families to celebrate together by the shore.

May 3–Sep 27

Sundays in the Shade at James River Cellars Winery

Sundays in the Shade at James River Cellars Winery

Well-behaved, leashed pets are invited to join their owners at this weekly event. Two- and four-legged friends can unwind outside under the pavilion while listening to live music and sipping various wine options. Bring a lawn chair or blanket and settle in for a cozy, laid-back vibe.

Sep 25–27

Dock Dogs at Neptune Festival Boardwalk Weekend

Virginia Beach, VA

Dock Dogs at Neptune Festival Boardwalk Weekend

Dock Dogs is a dock‑jumping competition featuring Big Air, Speed Retrieve and Extreme Vertical divisions where teams of handlers and dogs compete on a temporary pool set up on the beach. Spectator viewing is free and the event takes place on the Virginia Beach Oceanfront at 14th Street as part of Neptune Festival’s Boardwalk Weekend. The event’s organizer and DockDogs both state that anyone may bring a dog to compete and that viewing is open to the public.

Oct 3

Howlin' Coyote Canicross 10K Trail Race

King George, VA

Howlin' Coyote Canicross 10K Trail Race

Join this nonprofit trail race featuring challenging, varied terrain where leashed dogs (6-foot maximum) can run alongside their owners. The race is disposable cup–free, with runners receiving a SpeedCup or using their own hydration. Proceeds support park improvements and educational programming, with potential swag for both humans and pups.

Oct 24

Annual Outer Banks Brewtag

Annual Outer Banks Brewtag

A celebration of flight and beer, OBX Brewtag contestants will be competing to see who can launch and fly an empty 1/6 keg barrel the furthest. Dogs must be leashed and picked up after. A crafty selection of local and regional beer and food will be available for purchase that day.

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Cape Charles, VA, US