We love Pickleball!

Kent Island Classic Tournament

Tournament Sponsors 2024

At Chesapeake Pickleball, my mission is to provide high-quality instruction, as well as video analysis for implementing a personal strategy plan to make you a better player!  I will develop a personal plan through tactics as well as techniques to make your journey fun!

Located on Kent Island in Stevensville, MD and easily accessible from the first exit off of 50 after crossing the Chesapeake Bay Bridge from Annapolis, The Kentmorr Beach Bar & Grill boasts two dining rooms, an indoor bar, outdoor deck seating, and its very own private beach with beachside tiki bar. The restaurant has ample parking for both cars and boats.

Physical Therapy at Leah Ashlee Therapy is a cornerstone service dedicated to individuals looking to overcome injuries, manage chronic conditions, or improve mobility and balance. Unlike conventional fitness programs, Personal Training at Leah Ashlee Therapy is specifically tailored to aging adults who wish to stay active, build strength and improve their overall health. Leah’s approach is supportive, empowering clients to safely push their limits within a judgment-free environment.

First National Bank (FNB), one of the region’s leading full-service banks, has been committed to residents and businesses in the communities it serves for 150+ years. FNB provides leading-edge products and services delivered by local employees with local-decision making.

Discover Blue Heron Landing, a boutique bed and breakfast on Kent Island, perched on the shores of the Chesapeake Bay. Enjoy stunning views and a tranquil setting, or explore the vibrant local area. Choose from well-appointed rooms, suites, or a private cottage, and indulge in an abundant continental breakfast featuring local specialties. Experience Eastern Shore hospitality with personalized service and thoughtful touches ensuring an unforgettable stay.

The Winery is a family owned and operated premier liquor store located on Kent Island, Maryland. Voted "Best Retail Wine Selection" by What's Up Eastern Shore, the shop’s success is built upon providing exemplary customer service and an outstanding product line. The Winery offers a superb selection of wines, spirits, Champagnes, imported & craft beers, cigars and gourmet food. The Winery takes the intimidation out of shopping for wines, beers and spirits.