Weekend Activities


The Tour de Chesapeake is so much more than just a ride around a small town on a Saturday.  We have lined up a whole assortment of things for everyone (including non-riders) to do before, after and during the ride too.  We hope you will make a weekend of it and see all Mathews has to offer.

Friday, May 18, 2018:

10 a.m.-7 p.m.Local merchants on Main Street keep their doors open late for your convenience.

5-6:30 p.m. – East River History Tour by Mathews Deadrise Charters – $40 per person, max 6 passengers – Tour the East River’s historic homes and waterfront, explore the world of oyster aquaculture and even learn how to shuck the Chapel Creek Oyster – To register, contact Capt. Trey at 804-815-6132 or trey@shuckum.com.  www.chesapeakebayboattours.com

10 a.m.-8 p.m. – The Bay School Community Arts Center on Main Street will keep its doors open until 8 p.m. for a viewing of the “Art Speaks on the Bay” statewide juried art show. A wine tasting by Caret Cellars will also be available. *6:00 and 7:30 p.m. – Join Art Speaks Gallery coordinator, Saraya Cheney, for an exploration of contemporary art in Virginia.

Saturday, May 19, 2018

9 a.m.-1 p.m.Farmers Market – located on the Court Green – Fresh veggies, breads, muffins, soup, granola, and more – grown and made in Mathews!

9 a.m.-4 p.m. – Chesapeake Bay Paddling Company will be at Williams Wharf (Lunch site) offering “sea trials” for anyone interested in trying out a kayak or paddle board, as well as conducting kayak rolling demos every two hours (times announced on site).

10 a.m.-4 p.m. – 7th ANNUAL “ART deTOUR” – The artists of the Art deTour will gather on Main Street around The Bay School Community Arts Center to exhibit and sell their fine art and handcrafted works. Whether on bike or foot, this new venue will provide visitors the chance to browse and shop all in one place!

10 a.m.-7 p.m. – Visit our local merchants for some excellent shopping on Main Street and beyond (see Local Shopping); Free art demonstrations at Put-In Creek Carvings, Main Street, 725-3326; Buy fresh local seafood from Island Seafood, Risby Town Road, Gwynn’s Island (725-4962, Open Sat 9-5) or from the trucks on Main Street (yes, we’re serious; it’s as fresh as it gets and you’ll have a good story to tell your friends!)

5-9 p.m. – SATURDAY NIGHT SEAFOOD FEAST AND PARTY AT THE WHARF – Williams Wharf Landing, Rt. 614

  • Fresh seafood by Creekside Dining.  Menu TBA –  Available for purchase on site – this company takes credit cards.
  • Beer, Wine and soft drinks by the Mathews Visitor Center – Cash only please
  • Entertainment/Dancing provided by “Lynda Smith & 7th Street”

Sunday, May 20, 2018


6:30-8:30 a.m. – Coffee and Donuts available at THMS (donation requested to benefit local church)

Try our new Sunrise Pancake and Waffle House on Main Street next to Mi Casa Azteca! OR try one of our local restaurants open for breakfast on Sunday – Lynne’s Family Restaurant, Route 14/198, Hardee’s or Subway. Southwind Pizza is now open for Sunday Brunch at 9 a.m. For Restaurants open later, see “Local Eats”.


9-10 a.m. – East River History Tour by Mathews Deadrise Charters – $35 per person, max 6 passengers – Tour the East River’s historic homes and waterfront while enjoying a complimentary cup of premium coffee – To register, contact Capt. Trey at 804.815-6132 or trey@shuckum.com. www.chesapeakebayboattours.com

10 a.m. AND 2 p.m. – Guided Kayak Tour to New Point Lighthouse by the Chesapeake Bay Paddling Company – $40 per person, max 4 people – 2-2.5 hours – To register, contact Jim Warwick at 703-283-0619, lewesbound@gmail.com, or visit his booth at registration on Friday and Williams Wharf on Saturday.

“No Frills Rides” – Ride routes not yet experienced like Gwynn’s Island (Gwynn’s Island Museum) or Mobjack (The Poddery) The Poddery, located at 177 Poddery Lane, Foster, VA 23056, as well as Williams Wharf, THMS and the Gwynn’s Island Museum, welcome visitors to “park and ride” on Sunday.

Sunrise to Sunset – Launch your own personal kayak, canoe or any non-motorized watercraft from the floating docks at Williams Wharf Landing (Route 614 – 804-725-9685) and take a nice tour of the East River and Mobjack Bay. www.mathewslandconservancy.com

See Mathews by WaterVisitMathews.com – Boating & Boat Tours in Mathews


9 a.m.-4 p.m. – Visit the Mathews Co. Visitors Center and Put-In Creek Carvings on Main Street, as well as other local merchants (see Local Shopping)


1)    Mathews Market Days – Annual hometown festival held on the Friday and Saturday after Labor Day each year.  Craft booths, Food, Games, 5K Race, Entertainment, Poster contest, Bake/Craft/Canning Contests and more!  www.mathewsmarketdays.com 804-725-7196

2)    Gwynn’s Island Festival – Held the last Saturday in June each year.  The annual Chicken Dinner is Friday night from 4-7 p.m. and Festival Activities take place on Saturday from 9 a.m.-3:45 p.m.  For information, call Cricket Call at 804-725-7577.

3)    Mathews Community Yard Sale – Held the Saturday after Memorial Day each year from 8 a.m.-2 p.m.  Over 20 locations around Mathews take part selling antiques, collectibles and treasures you never knew you needed!  Maps and information are available at the Visitor Center.  Call for details 804-725-4229.

4)    Open Studio Tour – Held the Friday and Saturday after Thanksgiving each year from 10 a.m.-5 p.m.  Over 12 of Mathews’ leading artisans invite you to experience the intimate spaces and places that inspire their vast and varied collections of art.  Visit www.madeinmathews.com for details.

5)    Williams Wharf Landing – This “gem” of Mathews is owned by the Mathews Land Conservancy and hosts a variety of events annually, such as Crew Regattas, Open Water Swims, Running Races, Sailing Camps, Summer Outdoor Concerts and much more.  Visit www.mathewslandconservancy.com for event lists.

Check the  VisitMathews.com – Community Calendar for a full list of County happenings