Tour de Chesapeake Weekend in Mathews
May 16, 2026
Each May, Mathews comes alive with cyclists, coastal views, and small-town charm during the beloved Tour de Chesapeake. Now in its 27th year, this relaxed, scenic ride draws hundreds of cyclists and their families to Virginia’s Middle Peninsula for a weekend that feels equal parts event and getaway.
Flat, quiet roads wind past creeks, farmland, and open water at nearly every turn — making this one of the most approachable and picturesque cycling events on the East Coast. It’s easy to see why riders return year after year.
What to Expect on the Tour 
The Tour de Chesapeake is known for its easy terrain and breathtaking scenery. Multiple route options allow riders to choose their distance, with many routes traveling along Gwynn’s Island, Bethel Beach, and New Point Comfort.
Along the way, cyclists enjoy:
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sweeping Chesapeake Bay views
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peaceful country roads
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abundant birdlife and wildlife
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photo-worthy coastal landscapes
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welcoming rest stops and local volunteers
It’s not unusual to slow for a deer crossing or a flock of wild turkeys — just part of riding in Mathews.
Saturday Ride Day Highlights
Saturday’s fully supported ride includes rest stops, scenic pauses, and community gathering points throughout the county. Event headquarters is located at Thomas Hunter Middle School, with additional activity at Williams Wharf.
Riders can also enjoy:
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breakfast and lunch options
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SAG support along routes
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optional wellness and recovery offerings
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the unique mid-ride water crossing between Williams Wharf and Mobjack
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live music and waterfront atmosphere
(An alternate land route is available if you prefer to stay on wheels.)
More to Enjoy All Weekend
The Tour is more than a ride — it’s a full Mathews experience. Throughout the weekend you’ll find:
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Art deTour open studios and exhibits
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Mathews Farmers Market on Saturday morning
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coastal shopping and galleries
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local seafood and waterfront dining
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the lively Party at the Wharf on Saturday evening
Williams Wharf Landing, just minutes from the Inn, hosts the Saturday night celebration with music, food vendors, and sunset views over the East River.
Make It a Cycling Getaway
Many riders choose to turn Tour weekend into a full coastal escape — arriving early or lingering after the ride to unwind.
At The Inn at Tabbs Creek, guests can:
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cool off in the pool after a day on the bike
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relax in a quiet waterfront setting
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soak in a jetted tub in select suites
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enjoy peaceful mornings before ride day
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return after the Tour to refresh before evening festivities
It’s the perfect balance to an active day on the road.
Plan Your Tour Weekend Stay
Tour weekend is one of Mathews’ most popular spring events, and accommodations fill quickly throughout the county.
If you’re planning to ride, we recommend reserving early and making the most of the weekend — on and off the bike.
Book your stay and experience the Tour de Chesapeake at a slower, more scenic pace.
