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Rams's Head Inn
Ram Island,Shelter Island
631-749-0811

http://www.shelterislandinns.com/
The Ram's Head Inn is an inviting seaside getaway on Shelter Island with a relaxing atmosphere, gracious country accommodations, and world class dining and wines, year round. Its stunning and private location has made it a popular site for weddings, business retreats, and other private functions. Throughout the year, the Ram's Head Inn hosts many popular events, including wine dinners, a winery tour weekend, holiday events, and live jazz.

Pridwin Hotel
Crescent Beach,Shelter Island
631-749-0476

http://www.pridwin.com/
Featuring a dining room overlooking the bay. During the week, the Pridwin’s Wednesday evening cookouts, followed by live music and dancing are legendary. On weekends, experience "The Shelter Island Sound," music from Motown to Ibiza, featuring special guest DJs and a chance to dance poolside under the stars. All week long, the Pridwin Bar & Lounge specializes in frozen drinks and local wines.

The Dory Restaurant
The Dory Restaurant
Bridge Street,Shelter Island
631-749-8871

Serving lunch and dinner in season, featuring indoor and deck dining. Bar open year-round.

The Chequit Inn
23 Grand Avenue,Shelter Island
631-749-0018

http://www.shelterislandinns.com/
The Chequit Inn, built in 1872, is a charming Victorian country inn on Shelter Island. Located in the island's historic district, Shelter Island Heights, it has a lively downtown atmosphere, superb restaurant that is open daily year round with an extensive wine and beer selection, & accommodations. The Chequit Inn is accessible by public transportation.

Sunset Beach Restaurant & Hotel
35 Shore Road,Shelter Island
631-749-3000

http://www.SunsetBeachLI.com
Open Memorial Day to Labor Day, featuring deck dining and cocktails overlooking Shelter Island Bay.

 

Shelter Island Nightlife & Shelter Island Bars

 
 
 

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