For decades, the Inn at Longshore was a highly sought after wedding venue.
The ballroom, the lawn out back reaching to the Sound, the chance for the bridal party to stay in a charming New England inn — it was all there.
The Inn was also a popular choice for corporate events, fundraising galas, family celebrations — an all-purpose property.
Yet there was always something a bit off.
You couldn’t quite put your finger on it. But now that the Inn at Longshore has reopened — following a year-long renovation — you can see that relatively small changes are a very big deal.

Newly renovated Inn at K
The waterfront location is a major draw. But standing inside the ballroom before, you wouldn’t know it was there.
A stage — with curtains behind it — blocked it.
Now the stage is off to the side. Walking into the ballroom, the first thing you see is a view all the way out to the water.
Designers even moved a beam near the entrance ramp (now steps). Most people won’t notice that difference. But it is dramatic.

The stage is gone. Now the view is all the way through, to the back. The ballroom holds 400 people for receptions, 300 for banquets. (Photo/Dan Woog)
Out in back, a broad new deck (with portable bars) invites attendees to flow between indoors and out. It’s a common amenity at country clubs — but missing from the Inn at Longshore for forever.
Weddings now take place on the lawn directly behind — not off to the side, near the tennis courts. The bride walks out from the ballroom, across the deck and down a few steps, making a dramatic entrance.

The splendor of an outdoor wedding.
The first wedding at the new Inn was held September 11. In the middle of my tour with Michael Ryan, managing partner of Longshore Hospitality group — the Delamar-affiliated group that has a 30-year lease with the town of Westport — the grateful mother of that bride stopped by with gifts for the staff. The wedding, she said, was “a dream” — even beyond her expectations.
Another wedding was held on Sunday, September 13. That morning, 7 inches of rain devastated Westport. The wedding was delayed by an hour, to 3 p.m. But it was held outside
The ballroom, deck and lawn (plus improved landscaping) are the most visible changes. (And some things have changed only slightly. The façade retains its traditional look. the porte-cochère was scaled back from its original size, and the stately tree at the entrance is still there.)

Rear view of The Inn at Longshore (center). Longshore Sailing School is on the right. (Drone photo/John Videler for Videler Photography)
But guests who stay on the Inn’s 2nd and 3rd floors will notice many differences too. (On weekends, they’re usually wedding parties. Weekday guests include business executives, travelers — and former Westporters, who want to relive the Inn experience when they return to their home town.)
The 11 rooms and 3 suites have been completely redesigned. Each is unique; all match include modern amenities, but with an old-time inn feel. Every 3rd floor room is dormered.
Room numbers were hand painted. And guests don’t have swipe cards — they’re given actual brass keys.

The Compo Suite
The “Lewis Suite” includes framed photos from the Inn’s long-ago start, as Frederick E. Lewis’ private mansion.
The bride’s suite — used by her party on the day of the wedding — was specially decorated by Serena & Lily.
The third floor honeymoon suite is named for Jay Gatsby. It has a particularly striking view — appropriate, because when F. Scott Fitzgerald rented a home on Compo Road South, it is believed his vista of the Lewis estate all the way to the Sound inspired some of his images in “The Great Gatsby.”
Sunlight glittering off the water fills every room facing the Sound. (The bathroom in one offers a particularly killer view.)

Room with a view. (All photos/Longshore Hospitality Group, unless otherwise noted)
All new state-of-the-art mechanicals ensure smooth operation.
All told, Longshore Hospitality spent $8 million more in capital improvements than they had committed to the town.
The Inn at Longshore is almost completely booked for weddings, through 2027. Bookings for 2028 will begin in November.
La Plage was closed during the renovation. Diners may not see many changes. But the kitchen is completely revamped, easing food prep for both the restaurant and ballroom catering.
Few towns own an inn and restaurant — let alone an entire country club.
For more than 60 years — ever since the town of Westport bought Longshore (paying $1.9 million, for the entire 169 acres) — officials have tried to make the Inn even more special than it is.
Finally, they’ve done it.
Enjoy a fundraiser in the new ballroom. Stay in a very cool room. Have a meal at La Plage.
And — starting soon — book your 2028 wedding there.
(To learn more about the Inn at Longshore, click here.)
(“06880” regularly covers Longshore, town restaurants, local businesses — and, like today, their intersection. If you enjoy stories like this, please click here to support our work. Thank you!)

Thank you thank you Dan for this fabulous update. Looking forward to an event and enjoying the newly renovated town mansion … Now I’m going to call it. The Gatsby mansion on Long Island. Sound 💃🕺💃🧡💜🥰
For the Westport history buffs, I researched the “Inn” in 2010 and found, after a backward deed search, viewing various historic maps (including a Fairfield County pictorial representation of c.1855), that the “Inn” was initially built in c.1846-1847 by David Bradley. This conclusion research report and Fairfield pictorial can be provided by request.
A great way to experience the new ballroom is the Thursday, November 5 Westport Uncorked Wine Tasting put on by the Westport Sunrise Rotary Club and the Westport Fine Wine Company. Tickets are available at: https://checkout.square.site/merchant/97T8TPKFQDCAF/checkout/LRIART62O7O4EB4ZP4U54HNF