The Top 20 Attractions around Shelter Island
There are plenty of places to see and visit around Shelter Island. Whether you love hiking or cycling, Shelter Island is a region where 20
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
Last updated: November 17, 2025
Shelter Island Heights
Highlight • Historical Site
Explore the Shelter Island Heights Historic District, lined with preserved Victorian houses and offering a glimpse into the island's past.
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Grace Estate Preserve
Highlight • Trail
Grace Estate Preserve, on Long Island, is a natural sanctuary, encompassing diverse habitats and scenic trails.
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Sag Harbor
Highlight • Settlement
Sag Harbor is a picturesque village on the East End of Long Island, New York. It boasts a rich maritime history dating back to the 18th and 19th centuries and …
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Gardiner Windmill and Rev. Thomas James Homesite
Highlight • Historical Site
The Gardiner Windmill and Rev. Thomas James Homesite in East Hampton, New York, are integral to the area's history. Erected around 1804 by Nathaniel Dominy V, the Gardiner Windmill, also …
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Custer Institute and Observatory
Highlight • Monument
Custer Institute and Observatory, established in 1927, opens exclusively on Saturdays from 7 p.m. to 12 a.m. for Saturday Night Observing. Long Island's oldest public observatory offers tours led by …
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Most popular attractions around Shelter Island
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Still not found the Highlight you’re looking for? See guides of the top attractions in other regions:
MelvilleCold Spring HarborLloyd HarborMontaukHuntingtonDix HillsAmityvilleHuntington StationWest HillsWest BabylonGilgoCenterportEast FarmingdaleIslipBay ShoreHalesiteHuntington BaySouth HuntingtonWest Bay ShoreBrightwatersFishers IslandDeer ParkNorth Bay ShoreBrentwoodEatons NeckAsharokenCopiagueFire IslandSpringsLindenhurstShelter Island HeightsNorth AmityvilleNorth LindenhurstGreenlawnNoyackNorthwest HarborWyandanchWheatley HeightsStony BrookStony Brook UniversityCentereachNorth HavenDering HarborVillage of GreenportOrientGreenport WestEast MarionSag HarborWest IslipSoutholdHead Of The HarborNissequogueSaint JamesBridgehamptonLake RonkonkomaEast NorthportElwoodAmagansettRonkonkomaGreat RiverEast IslipNorth SeaPeconicFort SalongaWainscottMiddle IslandEast Hampton NorthSagaponackNorthportCommackHampton BaysTuckahoeShinnecock HillsSouthamptonNorthamptonEastportManorvilleCalvertonSaltaireWater MillVillage of IslandiaNesconsetCentral IslipEast SetauketOld FieldSetauketHauppaugeSmithtownMount SinaiFlandersOak BeachBabylonLake GroveBayportSayvilleCaptreeCenter MorichesEast MorichesRocky PointVillage Of The BranchTerryvilleBelle TerreSeldenPort Jefferson StationPort JeffersonPoquottWading RiverKings ParkMontauk Point State ParkWesthamptonEast HamptonBaywoodCutchogueRidgeWest SayvilleOakdaleBaiting HollowBohemiaHolbrookNorth Great RiverIslip TerraceNorth BabylonEast QuogueMiller PlaceRiverheadRiversideMorichesYaphankCoramVillage of ShorehamShirleyMasticRemsenburg-SpeonkNapeagueEast ShorehamCamp Hero State ParkBlue PointSound BeachFire Island National SeashoreQuogueWesthampton BeachFarmingvilleHoltsvilleGordon HeightsHither Hills State ParkNorth Patchogue
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