The best road cycling routes around Southold
4.4
(5)
290
riders
17
rides
Want to go road cycling around Southold? We’ve reviewed all of the road rides around Southold to identify the best. Explore them all here, and find your perfect road cycling route around Southold.
Last updated: November 5, 2025
4.5
(2)
70
riders
1. Shelter Island Heights loop from Silver Beach
39.6km
01:44
270m
270m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
Easy
5.0
(1)
44
riders
2. Truman's Beach – Orient Beach loop from Greenport
34.8km
01:33
60m
60m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
Easy
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures in England and beyond.
Sign up for free
15
riders
3. Foster Memorial Bathing Beach – Sag Harbor loop from Greenport
164km
06:27
660m
660m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
Expert
5.0
(1)
15
riders
4. Roadbike loop from Shelter Island
18.6km
00:48
130m
130m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
Easy
8
riders
5. Marratooka Lake loop from Nassau Farms
50.4km
02:03
150m
150m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Intermediate
Sign up for free to see 13 more rides around Southold.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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
Browse the best Road cycling routes in other regions.
Fort SalongaEast NorthportDix HillsLake GroveIslip TerraceBohemiaConnetquot River State Park PreserveCentereachNorthportAsharokenElwoodLake RonkonkomaHuntington StationHalesiteHuntingtonHuntington BaySetauketSouth HuntingtonEast FarmingdaleEatons NeckBayard Cutting Arboretum State ParkWest SayvilleSaint JamesNissequogueHead Of The HarborOakdaleVillage of IslandiaCenterportGreenlawnSunken Meadow State ParkHolbrookNorth Great RiverCommackRonkonkomaShelter Island HeightsBrightwatersAmagansett National Wildlife RefugeAmagansettOld FieldCopiagueIslipHeckscher State ParkGreat RiverStony Brook UniversityFarmingvilleHoltsvilleGilgoNorthwest HarborEast QuogueEast IslipHither Hills State ParkShelter IslandStony BrookBay ShoreEast Hampton NorthCentral IslipEast SetauketPatriot'S Hollow State ForestJamesportBrentwoodNorth Bay ShoreWest Bay ShoreOak BeachBelmont Lake State ParkSeatuck National Wildlife RefugeMelvilleMontaukFire IslandWest BabylonBridgehamptonArthur Kunz County ParkEastport Pine Barrens State ForestSmithtownSuffolk County ParkEastportPeconicNesconsetSagaponackVillage Of The BranchKings ParkNorth AmityvilleRemsenburg-SpeonkWest Hampton DunesEast HamptonRiversideNorthamptonHampton BaysSans Souci County ParkSayville National Wildlife RefugeSayvilleBayportPatchogueNissequogue River State ParkElizabeth A. Morton National Wildlife RefugeWainscottAmityvilleLindenhurstBabylonQuogue Wildlife RefugeQuogueFlandersGreenport WestCaptreeConscience Point National Wildlife RefugeBlue PointWyandanchWest IslipShinnecock HillsSouthamptonNorth SeaCoramQuiogueWesthamptonWesthampton BeachHenry'S Hollow Pine Barrens State ForestDering HarborCalvertonSound BeachMiller PlaceWater MillEast MarionOrientOrient Beach State ParkRobert Cushman Murphy County ParkLloyd HarborBrookhaven Pine Barrens State ForestWest HillsLongwood Pine Barrens State ForestEast ShorehamCutchogueNapeague State ParkManorvilleMount SinaiBelle TerrePort JeffersonDeer ParkNorth BabylonWading RiverNorth LindenhurstWheatley HeightsCaptree State ParkFire Island National SeashoreCold Spring Harbor State ParkCold Spring HarborTuckahoeRidgeCalverton Pine Barrens State ForestBrookhaven State ParkVillage of ShorehamBaiting HollowSag HarborKatherine Ordway Wildlife RefugeNorth HavenSpringsEast MorichesCenter MorichesMastic BeachTerrell River County ParkTerryvilleRocky Point Pine Barrens State ForestVillage of GreenportCaleb Smith State ParkMasticMontauk Point State ParkRheinstein Estate ParkMontauk County ParkCamp Hero State ParkShadmoor State ParkGilgo State ParkMiddle IslandGordon HeightsEast Bartlett Pine Barrens State ForestHauppaugeShirleyPanamoka Pine Barrens State ForestNoyackBaywoodMorichesSeldenPort Jefferson StationCathedral Pines County ParkFishers IslandNorthvilleCarmans River Pine Barrens State ForestYaphankWertheim National Wildlife RefugeRocky PointMedfordBellportNorth BellportPoquottNapeagueBrookhavenOtis Pike Fire Island High Dune WildernessMattituckRiverheadAquebogueEast PatchogueNorth PatchogueWildwood State ParkNew SuffolkLaurelHallock State Park PreserveTarget Rock National Wildlife Refuge
Get ready to conquer new peaks
Sign up for Free