Darren's Guidebook
Area Attractions
The Nature Conservancy Mashomack preserve is a 10 minute bike ride from the house. There is parking should you go by car. Mashomack feature 11 miles of coastline and 2,350 acres of creeks, woodlands and fields. Walking trails are marked and allow the option of various distances for all levels of hiking. Consider packing snacks, water, bug/tick spray, sunscreen and possibly a walking stick. Unfortunately no dogs or bicycles are allowed on the trails.
70 locals recommend
Mashomack Preserve
79 S Ferry RdThe Nature Conservancy Mashomack preserve is a 10 minute bike ride from the house. There is parking should you go by car. Mashomack feature 11 miles of coastline and 2,350 acres of creeks, woodlands and fields. Walking trails are marked and allow the option of various distances for all levels of hiking. Consider packing snacks, water, bug/tick spray, sunscreen and possibly a walking stick. Unfortunately no dogs or bicycles are allowed on the trails.
Great farmers and craftspeople market on Saturday’s 9am-12:30 at the History Center. Good to get there early for fresh foods and handmade items. Walk around the beautiful grounds of the historical society while there.
Havens Farmer's Market
16 S Ferry RdGreat farmers and craftspeople market on Saturday’s 9am-12:30 at the History Center. Good to get there early for fresh foods and handmade items. Walk around the beautiful grounds of the historical society while there.
The Perlman Music Program
73 Shore RdLocated across the road from where you will stay is Sylvester Manor Educational Farm which is dedicated to bringing sustainable agricultural practices to Shelter Island. The manor encompasses 235 acres of fields, forest, gardens and estuaries. Check the website for programs, events and workshops throughout the season. There are some open trail areas to walk leashed dogs.
The farm and farm stand feature fresh just picked produce, eggs and many products from local suppliers. This is a 5 minute walk from the house -
18 locals recommend
Sylvester Manor Educational Farm
80 N Ferry RdLocated across the road from where you will stay is Sylvester Manor Educational Farm which is dedicated to bringing sustainable agricultural practices to Shelter Island. The manor encompasses 235 acres of fields, forest, gardens and estuaries. Check the website for programs, events and workshops throughout the season. There are some open trail areas to walk leashed dogs.
The farm and farm stand feature fresh just picked produce, eggs and many products from local suppliers. This is a 5 minute walk from the house -
Taylors Island
Shelter Island Historical Society
16 S Ferry RdIsland Beaches
Menhaden Lane is a scenic short drive or bike ride from the house. Beautiful place to watch the sun rise and walk the dog. Dogs are permitted as long as they are under control and be sure to clean up. A day or weekly parking pass is required if going by car and can be purchased at town hall. The access is very easy for all ages and abilities. No lifeguards are on duty.
Menhaden Lane Beach
Menhaden LaneMenhaden Lane is a scenic short drive or bike ride from the house. Beautiful place to watch the sun rise and walk the dog. Dogs are permitted as long as they are under control and be sure to clean up. A day or weekly parking pass is required if going by car and can be purchased at town hall. The access is very easy for all ages and abilities. No lifeguards are on duty.
Crescent Beach
Wades Beach
114 S Midway RdFood Scene
SALT Waterfront Bar & Grill
63 S Menantic RdGreat food, atmosphere and service. Everything is made from scratch using fresh local ingredients. Dining or just having a drink at the bar is a wonderful experience and you will never feel rushed. If you only go out to dinner once during your stay make it the Vine Street Cafe. Less than a 10 minute drive from the house. Be sure to make a reservation.
61 locals recommend
Vine Street Café
41 S Ferry RdGreat food, atmosphere and service. Everything is made from scratch using fresh local ingredients. Dining or just having a drink at the bar is a wonderful experience and you will never feel rushed. If you only go out to dinner once during your stay make it the Vine Street Cafe. Less than a 10 minute drive from the house. Be sure to make a reservation.
The Rams Head is a great place to have lunch out on the lawn and enjoy the beautiful water view. I have not had dinner there however hear that it is very good. This is about a 10 minute drive from the house. If you go by bike you can coast downhill for a good distance and when you reach the top of the hill stop at the bar and have a cold beverage.
19 locals recommend
Ram's Head Inn
108 S Ram Island DrThe Rams Head is a great place to have lunch out on the lawn and enjoy the beautiful water view. I have not had dinner there however hear that it is very good. This is about a 10 minute drive from the house. If you go by bike you can coast downhill for a good distance and when you reach the top of the hill stop at the bar and have a cold beverage.
Stars has the best coffee on the island hands down! The owner Pepe takes great pride in his special blends and always makes you feel welcome. Great assortment of fresh muffins or egg burrito’s. My go to is the “Morning Burrito” with fresh avocado and the Shelter Island blend coffee. This is a gathering spot for many of the locals year round.
22 locals recommend
Stars Cafe
17 Grand AveStars has the best coffee on the island hands down! The owner Pepe takes great pride in his special blends and always makes you feel welcome. Great assortment of fresh muffins or egg burrito’s. My go to is the “Morning Burrito” with fresh avocado and the Shelter Island blend coffee. This is a gathering spot for many of the locals year round.
Maria's Kitchen
55 N Ferry Rd
The Pridwin
81 Shore Rd
Shelter Island Craft Brewery
55 N Ferry RdShopping
IGA Shelter Island
75 N Ferry Rd
Shelter Island Heights Pharmacy
19 Grand Ave
Bliss' Department Store
186 N Ferry Rd
Shelter Island Hardware
4 Grand AvenueIce Cream
Tuck Shop
75 N Menantic Rd
Shelter Island Whale's Tale
3 Ram Island RdRentals
Piccozzi's Bicycle Rental and Repair
175 North Ferry Road
Shelter Island Country Club
26 Sunnyside Ave