I am a homegrown Long Island gal and I am ashamed to say I've never been to Shelter Island! I heard from a few friends that Mashomack Preserve was a nice spot for a hike so we packed up and off we went! It really was a beautiful place to hike around. Great place for kids as some of the trails can be quite short if your family isn't ready to do too many miles yet.
𝑭𝒖𝒍𝒍 𝑴𝒂𝒔𝒉𝒐𝒎𝒂𝒄𝒌 𝑷𝒓𝒆𝒔𝒆𝒓𝒗𝒆 𝑹𝒖𝒏𝒅𝒐𝒘𝒏
- Free entrance and free parking
- Bathrooms are temporarily closed as is the main house
- The beginning of the trail involved several steps and there are many tree roots along the path. If you have a toddler/little just be cautious you may need to hold their hand. Once past this point, it becomes flat and easy.
- The red frog trail is the shortest at 1.5 miles and has a storybook along the trail to read a page every few minutes down the trail. With my 4 and 5 year old we managed to do more than 2 miles, completing the yellow butterfly trail.
- There are benches and places to take a water or snack break along the way
- There are saltwater wetlands here so even though we didn’t see or get any bugs or ticks, we doused ourselves in bug spray before we started
- We got to see some swans, crane, chipmunk, bunny, squirrel, and crickets during our walk
- Truly was a beautiful environment and a bit different because of that than other places we have been
- There were not many people but social distancing is required.
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About the Ferries
North Ferry: Dock from Greenport to the north side of Shelter Island.
- Same day roundtrip fare: $18 car/driver then $4 round trip any passenger 12+.
- The ferry ride is ongoing through most of the day and we didn’t need a reservation and we didn’t wait more than a couple of minutes to board.
- The ferry runs every 10-15 minutes throughout the day.
- The ferry trip itself took 9 minutes.
- There is nowhere else to sit. You remain in your car.
South Ferry: Dock from North Haven to the south side of Shelter Island.
- Same day roundtrip fare: $20 for car/driver then $3 any additional passenger
- The ferry ride is ongoing through most of the day and you don't need a reservation but you can buy your tickets online.
- The ferry runs every 10-15 minutes throughout the day.
 Photo of the North Ferry passing us while on our journey |  |
Please note that some things on Shelter Island may be seasonal. Please confirm a business is open before venturing out.
Places to Eat
Slice Pizza: 3 North Ferry Road, Shelter Island
Closed Mondays.
Not just your typical pizzeria. Serving up other favorites such as sandwiches, starters, and salads.
(631) 749-9292
Kyle's: 27 North Ferry Road, Shelter Island
Open Weekends with some take out available during the week.
Local place for breakfast, brunch, and bakery items. Please note you may have to pre-order 24 hours in advance. Call them to check.
(631) 749-0579
Stars Cafe: 17 Grand Ave, Shelter Island Heights
Open 7 days a week.
Breakfast and lunch as well as pastries, coffee, smoothies and more.
(631) 749-5345
The Islander: 63 N Ferry Road, Shelter Island
Classic comfort food for the whole family
(631) 749-1998
Things to Do
Shelter Island Whale's Tale: 3 Ram Island Road, Shelter Island
Seasonally open typically from Mother's Day to Columbus Day. Open 7 days a week from Memorial Day to Labor Day. Call for current hours.
This is a great place for families visiting Shelter Island. With a mini-golf course, ice cream, kid-friendly food, arcade, and more, this will be a great addition to your day on Shelter Island.
(631) 749-1839
Sylvester Manor Educational Farm: 80 North Ferry Road, Shelter Island
This is a 243-acre historic plantation meant to engage those of all ages in farm-based and cultural programs. Please note that the manor house is currently closed due to COVID-19.
This looks like another beautiful place to go for a walk during your day trip. Their farm stand is located at their Windmill Field, 21 Manwaring Road. There you can see pigs and chickens as well as featuring products from other local vendors. Find their map here.
(631) 749-0626
Reel Point Preserve: Click here for location
This is a beautiful wildlife habitat located on the edge of Ram Island on Shelter Island. However, it is being threatened due to erosion. The peninsula is a haven for migratory birds and butterflies, including osprey, piping plovers and Monarchs.
(631) 283-3195
Shelter Island Beaches: Beaches are for residents only. There are NO day passes in 2020 due to COVID-19. Normally, you can purchase a day pass from the Shelter Island Town Hall. If you are staying at a hotel, you can buy a weekly or monthly pass. You can reach Town Hall at (631) 749-1166 to see if their procedures have changed.
- Crescent Beach (Lifeguards, comfort station)
- Wades Beach (Lifeguards, comfort station)
- Shell Beach (No Lifeguards)
- Menhaden Lane Beach (Town Landing)
- Wades Beach (Lifeguards, comfort station)
- Crescent Beach (Lifeguards, comfort station)
