Trail News

Virginia’s Water Trails packed with fun events this paddling season

March 15, 2022

If you’ve been thinking about planning a getaway to paddle some of Virginia’s Water Trails, but you haven’t yet chosen when to go, consider planning your trip to coincide with a race, a fundraiser, or a festival!

April 2 & 3: Stratford Hall Wine & Oyster Festival

Located on the Northern Neck, Stratford Hall was established in the 1730s by the Lee family.  It is now a National Landmark, preserving the history of the Lee family, as well as the site’s women, and enslaved and indentured laborers. During the first weekend in April, Stratford Hall will be holding their Wine & Oyster Festival, featuring local wineries, breweries, seafood, and artisans.

logo for chincoteague seafood festival with shrimp, oysters, beer, and a lighthouse

May 7: Chincoteague Seafood Festival

If you’re looking for a seafood festival on the Eastern Shore, be sure to grab tickets to the Chincoteague Seafood Festival in advance, as they sell out quickly! Parking is limited so taking a shuttle is essential. But if you’re feeling adventurous, the venue does have a boat ramp, so choose from any of the launches on the island and paddle on over!

tents and vendors set up on lawn in front of historic building

May 28: Art & Music on the Farm

Hosted by the Barrier Islands Center on the Eastern Shore, this one is fun for the whole family! Enjoy live gospel, folk, and bluegrass music, peruse pieces from local artists and artisans, taste some local wine, and get the kiddos involved in their own art activity.

June 4: Clean the Bay Day

Help clean Onancock Creek by kayak, canoe or boat during the Chesapeake Bay Foundation’s 33rd annual Clean the Bay Day. Bring your own watercraft, or reserve a free kayak through Burnham Guides at [email protected] or 757-710-5137.

a small group of people walk down a pathway to tented vendors with big green trees all around

June 4 & 5: Arts in the Middle

Conveniently located on the Middle Peninsula in Urbanna, this 2-day festival is a celebration of all forms of art in Virginia’s River Realm. Come for live music, fine arts, local cuisine, and literary arts. If you stay the whole weekend, be sure to explore the Urbanna Creek Water Trail one morning!

June 11: Paddle Round the Island

If you haven’t yet explored the water trails of Chickahominy Riverfront Park, join hundreds of other paddlers in the 2nd Annual Paddle Round the Island race, hosted by Paddle On of Williamsburg, to benefit Tidewater Wildlife Rescue. The course meanders through stunning marsh creeks, packed with wildlife!

June 11 & 12: KayaXpedition

If you’re going to be closer to Chesapeake, VA, we highly recommend attending the KayaXpedition. Hosted by the City of Chesapeake, this event is open to all skill levels, so bring the whole family! There will also be live music, food trucks, and local vendors.

June 18: Pipeline Paddle for a Cure

Planning on paddling in Virginia Beach? Be sure to sign up for this event, to benefit the Cystic Fibrosis Foundation. Paddle the calm waters of Back Bay on either a 5 or 10-mile course, and then enjoy a post-paddle lunch at Blue Pete’s restaurant.

June 18: Le Tour De Shore

If you need a break from paddling (wait, is that possible?), you’ll definitely want to check out the Eastern shore’s bike ride. Choose anywhere from a 25K to 100 mile ride, and end your adventure with a BBQ lunch in Onancock.

a dozen horses walking in deep water in the foreground with kayakers in the background

July 27: Chincoteague Pony Swim

Witnessing the famous Chincoteague Pony Swim is an extremely memorable experience. But how about from a kayak? It can be tricky with parking, boat traffic, and large crowds, so if that stresses you out, you may want to watch from land. But if you’re up for an adventure, there are some helpful tips in this post from the Chesapeake Paddlers Association.

September 10: Portsmouth Paddle Battle

Support Portsmouth’s local maritime and naval history by participating in this paddling race. The event will have both kayak and SUP divisions, and ends with live music, food, drinks, and lots of family fun!

October 30: Halloween Paddle on Onancock Creek

Calling all witches, warlocks, and pirates, on kayaks or SUPs! This FREE event is a great way to close out the paddling season (rentals available for a small fee) on the Eastern shore.

urbanna oyster festival logoNovember 4 & 5: Urbanna Oyster Festival

Local beer, wine, and oysters, plus a shucking competition, kids activities, live music, and a pre-festival oyster education day! The Urbanna Oyster Festival has got it all, so be sure to mark this event on your calendar, even if it’s too cold to paddle the water trails by November.

grapes and oysters

November 19: Taste by the Bay

Presented by the Lancaster County Chamber of Commerce, Taste by the Bay is an event on the Northern Neck that you don’t want to miss! Located at the Tides Inn on Carter’s Creek not far from the Rappahannock, it’s the perfect location for an elegant and delicious event, celebrating local wines, craft brews, local artisans, and live music.

If this list wasn’t enough for you, be sure to check the Virginia Water Trails EVENTS page, for more events added throughout the year.

Happy Water Trails!

About the Author: Laura Scharle lives on the Eastern shore of Maryland and is a frequent paddler in coastal Virginia. She is a Virginia certified ecotour guide and is an independent marketing contractor with a focus in ecotourism and heritage tourism. Laura can be reached through our Eastern Shore ecotour guide listings.

Virginia Water Trails Logo