The Top 16 Attractions around Southold
There are plenty of places to see and visit around Southold. Whether you love hiking or cycling, Southold is a region where 16
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 20, 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.
Tip by
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 …
Tip by
Sign up now to discover places like this
Get recommendations on the best single tracks, peaks, & plenty of other exciting outdoor places.
Sign up for free
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 …
Tip by
Mitchell Park
Highlight • Viewpoint
Enjoy stunning vistas of the Long Island Sound from the park's waterfront promenade. Breathe in the fresh sea air and let the gentle waves soothe your soul. Observe the colorful …
Tip by
Mashomack Preserve
Highlight • Forest
Nestled on Shelter Island, Mashomack Preserve is a 2,039-acre natural wonderland. It features diverse ecosystems from woodlands to tidal creeks, offering picturesque trails for hikers. Rich in biodiversity, it's a …
Tip by
Sign up for free to discover even more attractions around Southold.
Sign up for free
Already have an account?
Most popular routes around Southold
Most popular attractions around Southold
Get inspired with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures around London and beyond.
Explore more
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 ShoreHuntington BayHalesiteSouth HuntingtonBrightwatersWest Bay ShoreDeer ParkBrentwoodNorth Bay ShoreAsharokenEatons NeckFishers IslandCopiagueFire IslandShelter IslandSpringsLindenhurstShelter Island HeightsNorth AmityvilleNorth LindenhurstGreenlawnNoyackNorthwest HarborStony Brook UniversityCentereachStony BrookWheatley HeightsWyandanchNorth HavenGreenport WestEast MarionVillage of GreenportDering HarborOrientSag HarborWest IslipSaint JamesHead Of The HarborNissequogueBridgehamptonLake RonkonkomaElwoodEast NorthportAmagansettRonkonkomaGreat RiverEast IslipNorth SeaPeconicFort SalongaWainscottMiddle IslandEast Hampton NorthSagaponackNorthportCommackTuckahoeHampton BaysSouthamptonShinnecock HillsNorthamptonManorvilleEastportCalvertonSaltaireWater MillVillage of IslandiaNesconsetSetauketOld FieldEast SetauketCentral IslipHauppaugeSmithtownMount SinaiFlandersOak BeachBabylonLake GroveBayportSayvilleCaptreeEast MorichesCenter MorichesRocky PointVillage Of The BranchSeldenTerryvillePort Jefferson StationPoquottPort JeffersonBelle TerreWading RiverKings ParkMontauk Point State ParkWesthamptonEast HamptonBaywoodCutchogueOakdaleRidgeWest SayvilleBaiting HollowBohemiaHolbrookIslip TerraceNorth Great RiverNorth BabylonEast QuogueMiller PlaceMorichesRiversideRiverheadYaphankCoramVillage of ShorehamShirleyMasticRemsenburg-SpeonkNapeagueEast ShorehamCamp Hero State ParkBlue PointSound BeachFire Island National SeashoreQuogueWesthampton BeachFarmingvilleHoltsvilleGordon HeightsHither Hills State ParkNorth Patchogue
Get ready to conquer new peaks
Sign up for Free