WESTPORT–Scores of Westport Journal readers gathered Tuesday night at the Cedar Point Yacht Club to hear from experts on how to maximize their fun in Westport this summer. The experts covered watersports, sailing, dining and evening entertainment. The event was made possible by the event sponsor, the real estate agency KMS at Compass.

Watersports

David McPherson, the founder and owner of Sea Kayak CT, had news about paddling and kayaking on and around the Saugatuck. 

They offer a new Saugatuck Spillway Tour, during which kayakers head north up the Saugatuck until the brainy water from the sea meets fresh water.

The quad-pedal kayak, the Hobie Fiesta, is a new rental this year and allows groups of four to paddle with their feet. SUP Sunset Tours brings together standard stand-up paddleboarders and electric SUPs for beautiful, sedate tours to watch the setting sun.

“SUP and SIP” tours will feature stand-up paddleboarding followed by cocktails at The Whelk–dates TBA in June.

And, though it is not a summer activity, it will be a warm-weather activity: Sea Kayak Connecticut will arrange winter 2026/27 destination kayaking and paddleboarding in St. Croix, US Virgin Islands. Dates TBA in June.

Sailing

The evening’s host, the Cedar Point Yacht Club, provided a splendid view of the lower Saugatuck River on a beautiful, sunny evening. Two of their members, Stephanie Swann and Eric Helgesen discussed the club’s Women’s Sailing and Junior Sailing programs. 

Their junior sailing program is open to children 6-16 years of age, regardless of club membership. 

Non-member adults interested in crewing big boats during the Wednesday and Sunday evening races can register in the club’s crew finder.

Dining

Massimo Tullio–owner of The Whelk and Massi Co–recently spent two and half weeks eating his way across Italy and helping expand his repertoire of Italian soul food (not to mention his belt size). Though the new dishes are not ready for the Massi Co menu yet, they will represent many of the restaurant’s daily specials throughout the summer. Before the presentation, Tullio poured The Whelk’s Frogger cocktail (cucumber vodka, cucumber juice, ginger, lime) for the guests.

Evening Entertainment

Carleigh Welsh is the Vice President and Executive Producer at the Levitt Pavilion for Performing Arts. From late May into October the Levitt brings to Westport music, dance and comedy performances as many as six nights a week. The scores of free performances are made possible by the handful of ticketed events featuring A-list artists. 

The season will kick off on May 24 with Charlie Hall’s tribute to Miles Davis. June will feature, among others, Disco Biscuits, Dark Star Orchestra and Wynton Marsalis. July’s big ticketed event is Dogs in a Pile. And The Revivalists will return to the Levitt a decade after their first appearance.

Welsh was surprised to see that several guests had never visited the Levitt. She enthusiastically exhorted the crowd to either plan nights at the Levitt or to just drop by when the whim hits you. The Levitt adds programs as the opportunities arise, so the best way to keep up on the “rolling schedule,” Welsh advised, is to sign up for the Levitt’s email alerts here. 

Welsh also warned guests about predatory ticket resellers. These are automated bots that snarf up tickets from popular venues all across the country and then resell them at a significant mark-up.