High Season: Top-Notch Racquet Destinations in New York and Maryland

Tennis courts

For many, summer represents an opportunity to travel, discover new places, unearth new hobbies and spend quality time with family. For Cliff Drysdale Tennis’s seasonal locations, which open in the spring and conclude in the fall, summer is synonymouswith peak racquet season. Two such venues are Southampton Racquet Club in Southampton, New York and Inn at Perry Cabin, an intimate resort in St. Michaels, Maryland. Each of these locations afford players the signature CDT on-court treatment but offer unique experiences to recharge away from the bustle of day-to-day life.

Southampton Racquet Club

Each summer, international and domestic guests flock to the Hamptons for an oceanside escape complimented by historic charm, boutique shops, restaurants, vineyards and an endless calendar of social events that begin Memorial Day Weekend. Southampton Racquet Club, in its tenth season under Cliff Drysdale Management, is no exception to the inpouring of summer locals. Under CDM’s steward-ship, the seasonal racquet facility has grown immensely thanks to evolved programming, collaboration with the club’s parent property, and connections with local business owners and members of the community.

At the height of the summer season, Southampton Village buzzes with activity. Featuring art shows, movies and concerts in Agawam Park, a weekly farmers market, high-end fashion stores, and a wide variety of restaurants, visitors of all tastes can sample a variety of activities rain or shine.

The village is also home to a number of historical land-marks, including the house of Thomas Halsey, one of the founders of Southampton. Rebuilt by Thomas’s son in 1683, visitors today can take a tour of the original house and property. More modern landmarks include Tate’s Bakeshop, a bakery founded in 1980 by Kathleen Tate, as well as Sip n’ Soda, a local favorite among families for their breakfast and lunch offerings that was originally founded as an ice cream parlor in 1958. Rounding out the must-see list of sights is Cooper’s Beach, a widely known destination that has been recognized as one of the top 10 most beautiful beaches in the United States.

Group Tennis Event Picture

Conveniently located ten minutes from the lively village, Southampton Racquet Club (SRC) is nestled off the road within the surrounding wooded landscape. Perhaps the greatest benefit of SRC is that it is a public tennis club. Many clubs in the Hamptons are private venues exclusive to members, while SRC allows full-time guest access and reserves benefits such as complimentary court time, game arranging, member socials and club discounts for members.

“One of the most rewarding things about having been at SRC for so long now is seeing how much the club has grown,” said Senior Director, Elliot Pegg. “We have had a solid membership group that rejoins year after year since I arrived in 2015, in addition to new members and guests each season.

“We’ve also made a lot of improvements,” said Pegg. “Last season we put up a brand-new fence, and over the years we have updated our irrigation system, enhanced our program offerings and boosted our pro shop inventory. I am looking forward to hitting the ground running this season and welcoming back an impressive pro staff.”

SRC as a seasonal club has been uniquely fortunate to host familiar pros year after year, and the result has been a tight-knit team and a familial atmosphere among the staff and membership.

“From a client’s perspective, many players feel like they can pick up where they left off last summer when they see returning pros,” said Pegg.

Personally, Southampton has a very special place in my heart, as I spend my summers as the Club Manager. I am very proud of the environment we’ve created for people to come and play tennis. It means a lot when clients tell us that our courts are welcoming, fun and instructive. And to see how much the club has grown over the years is a big accomplishment for all of us. With quite a few more events on our social calendar this year, we are all looking forward to being back on the courts and giving all our clients that signature Cliff Drysdale Tennis experience.

Inn at Perry Cabin

The Eastern Shoreline is an undiscovered secret rich with charm, history, and hospitality, all of which you can experience for yourself at Inn at Perry Cabin. The Inn, located in St. Michaels, Maryland just across the Chesapeake Bay, used to be a 24-acre tobacco farm in the 1800s. Today, the Inn is a picturesque estate of 30 suites and 48 guest rooms overlooking the Miles River.

The resort’s 26-acre tract was gifted to Samuel Hambleton from Congress after the War of 1812 was won. He elected to name the manor after Commodore Perry whom he provided consul to during the war. When Hambleton passed away in 1851, the estate continued to serve as a farm for nearly a hundred years before it was transformed into a riding academy in 1952. The owners of the riding academy would then transform the resort into “a small holiday destination called the Inn at Perry Cabin.”

Inn at Perry Cabin ultimately become a resort destination known all over the world. Now as a member of Historic Hotels of America, the Inn at Perry Cabin continues to earn recognition as one of the top-rated historic venues in the Mid-Atlantic Region (and even served as the backdrop for the popular 2005 romantic comedy, Wedding Crashers). From the “story book setting” of beautifully kept grounds, amenities including daily activities for guests, world-class tennis instruction, golfing, biking, a luxurious spa, a 24-hour fitness center, and an unforgettable on-property dining experience, a visit to Inn at Perry Cabin is an absolute must.

Each year, the season opening is marked by “Return of the Fleet,” a full-day, kickoff celebration marked by a procession of the resort’s impressive fleet. What started out as an intimate soiree has evolved into one of Inn at Perry Cabin’s biggest events of the year.

Captain Jason Pinter, Inn at Perry Cabin’s Water Director, described the event as a “time for us to take off our winter coats and put our spring coats on. Inn at Perry Cabin begins to come alive in the spring and Return of the Fleet only helps to usher in the season.”

Walk Around The Garden

As a guest, you can charter your own day on the water, be it a private tour of the Miles River, a sunset sail or a group gathering in one of the fleet’s sailboats, motorboats or even a 40-foot yacht. In addition to private charters, Inn at Perry Cabin also has a Sailing Academy that offers everything from basic through multi-day sailing certification courses with the seasoned sailing instructors.

Other amenities include the Links Golf Course, infamously designed by Pete Dye as his final masterpiece. Snaking along a wooded property line, Links is designed for players of all levels to enjoy a challenging round within the Eastern Shore’s scenic landscape. Director of Links, John Mlynarsky, likened the course to Pete Dye’s mantra: “Keep it fun, keep it moving, and keep it beautiful.”

In addition to the course, Links now features eight advanced Golf Simulators, perfect for rainy days or a little technical practice. During the summer, Links also hosts a food truck on-site with fresh offerings courtesy of the Inn’s chefs.

Speaking of food, the Inn’s dining experience promises to be a memorable one. Each meal is prepared by award-winning Chef Gregory James, who was recently named Chef of the Year in Maryland. In keeping with Chef Gregory’s mission to source only the best and freshest offerings, the dinner menu changes on a daily basis and includes only local ingredients harvested within a 25-mile radius. Of course, a natural question is how Chef Gregory keeps things “fresh” (pun intended) with a new menu each day.

“When I have my ingredients for the day in front of me, my staff and I brainstorm menu ideas for dinner right then and there,” said James. “If we have leftover pork, we’ll make broth or ribs for the bar. If we can’t get a particular ingredient, then you won’t find it on the menu.”

Lighted Har Tru Tennis Courts

The other amenities in the resort’s repertoire echo the world-class standard, including a comprehensive racquet program by Cliff Drysdale Tennis. This season, England native Matt Kirkham has been named Director of Racquets in St. Michaels. A seasoned instructor with experience in both resort and private club venues, Kirkham has tailored a calendar of mixers, round robins and socials for guests and members of all levels to enjoy.

The racquet facility features three Har-Tru clay courts lighted for night play and are open to member and resort guest use on a seasonal basis.

If you’re looking for a fresh retreat that includes choice tennis instruction, incredible food, luxurious accommodations and pristine amenities, the Inn at Perry Cabin promises an unforgettable getaway. Book your stay today to experience the award-winning, premier resort on Maryland’s Eastern Shore.