The Pridwin Hotel and Cottages

Stay Dates & Guests

A Flag On A Flagpole

Fall Weekends at The Pridwin

Available Fall 2025

The Pridwin Hotel and Cottages

Every weekend this fall—daily traditions await, delicious dining invites, and new events pepper in excitement.

A magic golden glow-every weekend this fall.

Plan a fall escape to The Pridwin on Shelter Island, where crisp coastal air, vibrant foliage, and curated seasonal programming come together for the perfect East End getaway. Book a stay this September or October and enjoy classic autumn activities like s'mores by the fire, outdoor movies, kayaking, and live acoustic music.

Each weekend features a lineup of complimentary events and local experiences, including Friday culinary tastings in the Grove, Saturday wine tastings with vineyards like Wölffer Estate, Macari, and Palmer, as well as Peeko Oyster pop-ups on the lawn. Guests can also join short fishing charters with dockside cooking demos, explore Sylvester Manor on guided culinary tours, or take part in Chef Todd Ruiz's hands-on chicken feeding class. Family-friendly fun like pumpkin painting and cornhole tournaments round out the weekend. On Sundays, unwind with our new Sunday Supper Series-relaxed, chef-driven meals served on the lawn, celebrating the flavors of the season.

Included in your Fall Getaway

  • Deluxe Overnight Accommodations
  • Daily Deluxe Continental Breakfast
  • Daily Complimentary Guest Activities like S'mores on the Lawn, Pumpkin Painting, Culinary Gardening, Cornhole, Croquet, Kayaks, Fishing and more

Weekend Sample Itinerary

Thursday

A Group Of People Sitting On A Stage With A Large Screen
Check-In with Madeline Cookies and Warm Apple Cider
3:00pm
S’mores on the Lawn
6:00pm - 8:00pm
Family Movie in the Grove
7:30pm

Friday

A Fire Pit With A Flame
Yoga on the Lawn
8:00am - 9:00am
Art in the Grove
1:00pm - 3:00pm
Oysters and Bubbles on the Lawn
4:00pm - 7:00pm
S’mores & Smoked Whisky Cocktails in the Grove
6:00pm - 8:00pm

Saturday

A Garden With A Statue In The Middle Of It
Chicken Class with Chef Todd
10:00am-10:00am
Cornhole Tournament on the Lawn
1:00pm - 3:00pm
East End Wine Tasting on the Lawn
1:00pm - 3:00pm
Pumpkin Painting on the Lawn
2:00pm - 3:00pm
S’mores on the Lawn
6:00pm - 8:00pm
Concert in the Grove
7:30pm - 9:00pm

Sunday

A Group Of People At A Farmers Market
Rise & Revive Stretch Class
8:00am - 9:00am
Culinary Gardening with Chef Todd
11:00am-12:00pm
Pumpkin Painting on the Lawn
2:00pm - 3:00pm
Sunday Supper on the Lawn
5:00pm - 8:30pm
Cocktails in the Grove
8:30pm - 9:30pm

Available Daily

A Man And Woman Dancing In A Backyard
Bicycles
7:00am - 8:00pm
Cornhole
8:00am - 8:00pm
Croquet
8:00am - 8:00pm
Kayaks
10:00am - 8:00pm
Fishing
8:00am - 8:00pm
Moke™ Rentals
8:00am - 8:00pm
A Bowl Of Apples

Beat the crowds and experience fall on Shelter Island-peaceful, picturesque, and rooted in tradition at The Pridwin.

A Wedding Ceremony On A Beach
Special Events

Sunday Suppers at The Pridwin

This fall, Sunday afternoons at The Pridwin are getting a delicious new tradition. Join us on the lawn each weekend for the Sunday Supper Series-a relaxed, open-air dining experience that brings together great food, good company, and the best of the season.

Sundays from September 7 through October 19, 2025
5:00pm - 8:30pm

A Collage Of A Person Wearing A Garment
Special Events

Masquerade Ball

It will be quite a night this Halloween as The Pridwin transforms into the ultimate Halloween Party: The Masquerade Ball. Step into a world of mystery, elegance, and enchantment, where masks aren't just welcome-they're essential. Enjoy an evening filled with hauntingly beautiful décor, delicious seasonal fare, and live entertainment that will keep the energy high well into the night.

Friday, October 31, 2025

Request Information

For all inquiries for meeting rooms, weddings or events over 10 persons, please fill out the form below.
Wedding | Request For Proposal

Wedding | Request For Proposal