Road Trip: The Pridwin

Lynne Schur, Managing Editor

The Pridwin, Hamptons

What is it about fall that makes you want to get cozy? Well, the Pridwin — one of the buzziest openings in the Hamptons this past summer — may just be for you. Located on Shelter Island, it’s the quintessential historic inn, built in 1927. But don’t worry, it was gut renovated, top to bottom, with all the creature comforts. It still has a charm that inspires you to sit on an Adirondack chair for a beat.

Once November hits, so does the drive to, well…  drive. One of the best escapes to cure the November doldrums is hopping in the car and heading east — from New York City, that is. Because that’s where the Pridwin Hotel awaits. What more could you be craving than an autumn visit to the Hamptons, especially if your final destination is the quaint oasis of Shelter Island. It’s a healthy drive, and you’re heading toward the sea. And with each blowing leaf, the pre-holiday hustle of the city gets left further and further behind.

Why the Pridwin Hamptons

The Pridwin Resort Hotel and Cottages is making its long-awaited comeback, opening under new management for its 95th anniversary. Yes, you heard that right. This historic hotel, first built in 1927, had some bumps in its timeline recently, due to the pandemic. But now the restoration is complete. And it’s been done in a way that all full-on restorations should —by preserving the vibe, which is old-school, comfy, classic, and relaxed. But it also pumps up the luxe. And, the $28 million redevelopment project isn’t short on elegance.

Where you’ll stay and eat

The new Pridwin has 16 private cottages on seven acres, plus 49 guest rooms in the main building. Rooms have clean, nautical accents. If you’re looking for a little more elbow room than the resort rooms have to offer, try the cottages, which have roomy accoms that include private decks, separate living areas, and gas fireplaces.

An on-site restaurant, the Terrace, is the perfect water-view restaurant whose indoor dining flows out to the deck. The menu ingredients are sourced locally, with an emphasis on classic Long Island seafood. There’s also fall jazz and other live entertainment. 

What you’ll do

With the resort overlooking Shelter Island’s Crescent Beach, you’ll have your own private beach to explore, views of Peconic Bay, a pool (in season), as well as access to kayaks, paddle boards, and bikes (manual and electric). Fall is a special time to be here, with the Mashomack Preserve taking up about a third of the island and the natural resources in the area at their peak. There’s also a new spa addition at the hotel if you prefer to kick back on the property and enjoy massages and facials.

The Petry family has owned and operated the Pridwin since 1961, so they’re not short on legacy, knowledge, or stories about Shelter Island. Inquire while having a hearty glass of red wine on the terrace at sunset. The Madeira is a good fall choice.

Related Articles:

Road Trip: The Wauwinet

Where to Eat in the Hamptons

Fall NY Road Trips: Where to Stay

The Pridwin Information

Address: 81 Shore Road, Shelter Island, NY 11964-2009

Phone: 1-844-200-5001

Previous Post
Life House Berkshires
Next Post
Road Trip: Shou Sugi Ban House


Powered by Expedia

Previous Post
Life House Berkshires
Next Post
Road Trip: Shou Sugi Ban House




Book My Trip
The List

Galavante’s Picks for

Related Articles

Recent Articles

Shinjis NYC Bar

Abhilash Jayachandra, Editor

Cocktail Bars in NYC to Know

It used to be that heading to a bar for a nightcap was the afterthought for the evening. That was before it became an art to craft a cocktail and…
Round trip One-way Multi-city
No. of Adults (18 and older)
No. of Children (Age 2 through 17)
No. of Infants (Younger than 2) On lap In seat
Nonstop Refundable

Powered by Expedia

Book My Trip