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The Pridwin Hotel and Cottages

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The Perfect Fall Weekend

Available Weekends in Fall 2027 | September 30 to November 4

The Pridwin Hotel and Cottages

Come spend the weekend at The Pridwin, where we’ve planned the perfect fall escape for two.

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As the pace of summer softens and Shelter Island settles into its most beautiful season, The Pridwin invites you to embrace a new autumn tradition. Our Fall Weekends are thoughtfully curated escapes that combines luxurious accommodations with immersive experiences centered around art, food, nature, history, and discovery. Arrive and settle into island life with leisurely breakfasts, seasonal lunches, chef-driven dinners, and warm gatherings that bring guests together.

Included in this Package for Two Guests:

  • Early Access to The Pridwin property
  • Breakfast, Lunch, and Dinner each day, including a 5-Course Fall Harvest Dinner on Saturday evening showcasing local meat, fish, and produce—with wine pairings from Macari Vineyards. 
  • Sweets in The Grove
  • Live music and family-friendly entertainment
  • Includes access to all Resort Amenities
A Fire On A Road

Each weekend features a distinctive theme led by expert hosts, from artists and historians to naturalists and astronomers, offering opportunities to learn, explore, create, and connect in meaningful ways.

People Standing On A Beach
Fall Weekend Themes

Under the Island Sky

As daylight fades and the stars emerge above Shelter Island, discover the wonder of the night sky during a weekend devoted to astronomy and exploration. Guided by a visiting astronomer, guests will learn to identify constellations, planets, and celestial phenomena through engaging talks and hands-on discovery.

The experience culminates with an unforgettable evening of telescope viewing beside the water, where the expansive sky and tranquil setting create a sense of awe that feels uniquely Pridwin.

A Group Of Speakers In A Field
Fall Weekend Themes

Paint The Pridwin

Celebrate creativity in one of the East End's most inspiring landscapes. During this artistic retreat, a renowned visiting artist will guide guests through painting sessions designed for all skill levels, from beginners to experienced creators.

Alongside additional hands-on workshops and creative experiences, you'll draw inspiration from The Pridwin's waterfront setting while creating your own original work to take home as a lasting reminder of your Shelter Island escape.

A Bottle Of Wine Next To A Bouquet Of Flowers
Fall Weekend Themes

A Taste of the North Fork

Experience the flavors, stories, and people that define Long Island wine country. This culinary weekend brings together local vintners, producers, and The Pridwin's culinary team for intimate tastings, conversations, and unforgettable meals.

Discover exceptional regional wines through guided tastings and enjoy a special pairing dinner that celebrates the bounty of the North Fork, showcasing seasonal ingredients and the craftsmanship behind every bottle and plate.

A Body Of Water With Trees Around It
Fall Weekend Themes

The Wild Side of Shelter Island

Explore Shelter Island through the eyes of a naturalist and photographer. This immersive weekend invites guests to discover the island's remarkable wildlife, coastal habitats, and hidden landscapes while learning techniques to observe and capture nature's most compelling moments.

Through guided excursions and expert insight, you'll gain a deeper appreciation for the island's natural beauty and leave with both new skills and memorable photographs.

A Dock With A House On It
Fall Weekend Themes

From Shore to Table

Follow the journey of a local ingredient from its source to your plate in a weekend dedicated to culinary discovery. Meet the growers, harvesters, and producers who shape the region's food culture, then experience their stories brought to life through thoughtfully prepared meals.

Alongside Chef-led discussions and behind-the-scenes insights, guests will enjoy a special dining experience that highlights the connection between place, people, and exceptional cuisine.

A Group Of People Sitting On A Bench By A Body Of Water
Fall Weekend Themes

Secrets & Stories of Shelter Island

Step into the rich history of Shelter Island through a captivating weekend of stories, heritage, and discovery. Led by a knowledgeable historian, guests will explore the island's fascinating past, from its maritime roots and notable residents to the enduring legacy of The Pridwin itself.

Through talks, guided experiences, and engaging storytelling, you'll uncover the people, places, and mysteries that have shaped this remarkable destination for generations.

Stay in the know.

From new overnight packages, to exclusive dinners, to exciting seasonal celebrations. Be the first to know about what’s new at The Pridwin.

Return year after year and discover a new tradition every fall.

A Pool With Lounge Chairs And Umbrellas By It
P.S. A little bit of summer still lingers on Shelter Island. Our pool is heated, so pack your swimsuit.
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