Courtesy Ram's Head Inn

The Ram’s Head Inn has been offering world class accommodations and service since it was built in 1929.  The 15,ooo square foot building is all original outside, with 17 fully renovated guest rooms.  Sitting on over 4 acres of beautiful secluded land, your options for activities are only limited by your imagination.  Take out a kayak or a sailboat, go for a quiet walk, try outdoor yoga.  There’s also a regulation size tennis court, bocce ball, and a slew of yard games.  If you just want to relax, take a towel down to the 800 feet of private beach front, or laze the day away in a hammock.

Only 100 miles from New York City, the inn is accessible via ferry from either Sag Harbor or Greenport.  The concierge is at your service to plan day trips to North Fork vineyards, farmstands, pumpkin picking, the theater and antique shopping.  This season they’re offering some amazing fall specials.

Shelter Island Sunday Dine & Stay Package:

Spend a Sunday night at the Ram’s Head Inn this October* and enjoy pampering at its best. These special lodging rates below include a Room & Dinner for Two in their gourmet restaurant. 

Private Bath: $300/night

Shared Bath: $250/night

Two Bedroom Suite: $550/night

*Excludes holiday weekends.

Courtesy Ram’s Head Inn

Sunday Night Jazz:

Relax in the cocktail lounge, Harbor Hall, or watch the sunset on the Great Lawn to the sounds of live jazz from Jane Hastay, Peter Martin Weiss, their incomparable band, and their guest vocalists.

Sunday September 23rd & 30th at 6pm.   The final Jazz night of the season will take place on Sunday, October 7th, of Columbus Day Weekend.

Harbor Hall; Courtesy Ram’s Head Inn

Fall Friday Date Nights:

Prix fixe of $35++ per person, enjoy a special three course meal complimented with Harry’s specially priced wines from our list.   Live music in the lounge makes this the most romantic night on the island!

Starters include:

Fresh Tomato & Mozzarella Stack, basil chiffonade, balsamic glaze
Wedge Salad with dried cranberries, toasted pine nuts,crumbled bleu cheese, balsamic dressing
Beef & Shiitake Mushroom Soup

Main Dishes:

Chicken Osso Bucco-fusilli pasta
Herb Crusted Swordfish-lemon beurre blanc
Apple Cider Pork Chop, caramelized onion,  apple chutney


Panna Cotta with strawberry puree
Lava Cake

Courtesy Ram’s Head Inn

During your stay, don’t miss their signature fall cocktail crafted by their inhouse mixologist, Harry Brigham:  The Smashing Pumpkin

The Smashing Pumpkin

2 oz Soltado Spicy Añejo Tequila

2 oz Fresh Local Apple Cider

3/4 oz Pumpkin Spice Syrup

2 1/2 oz Shipyard Pumpkin Head Ale (or other pumpkin flavored beer)

Combine first 3 ingredients in mixing cup with ice, shake to chill, strain into chilled martini glass. Add pumpkin beer.  Garnish with fresh apple slice and a dash of nutmeg.

Ram’s Head Inn, 108 Ram’s Island Drive, Shelter Island Heights.

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