3.9
(8)
345
riders
70
rides
Road cycling routes around Smithtown navigate a landscape characterized by diverse ecosystems, including woodlands, wetlands, and river systems. The area features rolling hills and valleys, particularly around the Nissequogue River and within extensive parklands like Blydenburgh County Park and Caleb Smith State Park Preserve. These natural features provide varied terrain and scenic backdrops for road cyclists, with routes often traversing well-paved surfaces and offering moderate elevation gains.
Last updated: May 18, 2026
8
riders
78.6km
03:24
480m
480m
The Mount Sinai Harbor Loop is a moderate 48.8-mile road cycling route with scenic harbor views and 1581 feet of elevation gain.
23
riders
71.2km
03:28
650m
650m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Sign up for free
20
riders
47.3km
02:25
430m
430m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
11
riders
42.7km
01:59
300m
300m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(1)
25
riders
69.9km
03:09
600m
600m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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.
Start today with a free account
Your next adventure awaits.
Login or Signup
This beach is a nice spot for swimming, with restrooms, playground equipment, campsites and a refreshment stand. The water usually passes cleanliness standards.
0
0
These wetlands are designated as a state conservation area due to their important habitat for coastal fish and wildlife. Keep an eye out for abundant birds, including endangered species like the short-eared owl and pie-billed grebe. Although you're less likely to see them, the mudflats, channels, and wetlands also provide vital habitat for fish and marine invertebrates.
0
0
Avalon Nature Preserve, in Head of the Harbor, captivates with its diverse ecosystems. Spanning 216 acres, it features woodlands, wetlands, and serene trails, providing a peaceful haven for nature enthusiasts.
0
0
Situated on the western bank of the Nissequogue River, near its estuarine mouth, this 93 acre forested property is utilized primarily for hiking. Arthur Kunz County Park features tidal creeks, a lush, mixed deciduous forest, rolling hills and valleys, and quaint hidden ponds all of which provide important habitat for wildlife. The trail system in the park provides a scenic link in a section of the Long Island Greenbelt Trail which heads north from Arthur Kunz Park to its terminus at Sunken Meadow State Park.
0
0
Gorgeous views all around, very quiet and secluded. It'd be a lovely spot to have lunch and read a book. The roads there are very hilly and the town it's in is quite wooded and forest-y; it doesn't feel like the usual strip-mall suburbs of Long Island.
0
0
The lighthouse sits on the northern tip of Old Field. It was first built in 1823, then rebuilt in 1868. The U.S. Coast Guard took it during WWII but gave it back to the Old Field community afterwards.
0
0
Mount Sinai Harbor holds a marine sanctuary and a nature preserve. It's a beautiful place, popular with clamming and fishing enthusiasts.
0
0
There are over 60 road cycling routes around Smithtown, offering a variety of experiences for different skill levels. These include 16 easy routes and 50 moderate routes.
Smithtown's road cycling routes feature diverse terrain, including rolling hills and valleys, particularly around the Nissequogue River. You'll encounter woodlands, wetlands, and river systems, with many routes offering well-paved surfaces and moderate elevation gains.
Yes, many routes in Smithtown are designed as loops, allowing you to start and end at the same point. Examples include the Mount Sinai Harbor Loop and the Cordwood Park – Avalon Nature Preserve loop from Smithtown.
Road cycling routes in Smithtown often pass by significant natural features and parklands. You might cycle near the Nissequogue River system, through areas with views of the Long Island Sound, or alongside preserves like Avalon Nature Preserve and Blydenburgh County Park. The Old Field Point Light – Cordwood Park loop from Smithtown, for instance, leads through coastal areas.
The best time for road cycling in Smithtown is typically during spring, summer, and fall. These seasons offer pleasant weather conditions, with fall foliage providing particularly scenic backdrops along the Nissequogue River and within the various parklands.
While many routes feature moderate elevation gains, some sections of the Long Island Greenbelt Trail, which passes through Smithtown, incorporate quiet roads that could be suitable for families. For specific family-friendly paved paths, it's advisable to check local park regulations and trail conditions.
The road cycling routes in Smithtown are highly rated by the komoot community, with an average score of 3.5 stars from over 6 reviews. Cyclists often praise the varied terrain, scenic views, and the opportunity to explore diverse ecosystems like woodlands and river systems.
While specific cafes directly on every route are not detailed, Smithtown and its surrounding towns offer various amenities. Routes like the Mount Sinai Harbor Loop pass through areas where you can find local establishments for refreshments.
Many county and state parks in Smithtown, such as Blydenburgh County Park and Caleb Smith State Park Preserve, offer designated parking areas that can serve as convenient starting points for road cycling routes. It's recommended to check specific park websites for parking availability and any potential fees.
Public transportation options to access specific trailheads in Smithtown may be limited. It's best to research local bus routes or train services (such as the Long Island Rail Road) to nearby towns and then plan your cycling route from there, considering the distance to the starting point.
While most routes are classified as moderate, some offer more significant elevation gains and longer distances. For example, the Allsop-Fisher Saltmarsh – Mill Pond loop from Kings Park covers over 100 km with substantial climbing, providing a more challenging experience.
Many routes offer scenic viewpoints, particularly those that traverse coastal areas or higher elevations. The bluffs within Sunken Meadow State Park, accessible from some routes, provide stunning views of the Long Island Sound and Connecticut. Routes near the Nissequogue River also offer picturesque vistas, especially during fall foliage.


Browse the best Road cycling routes in other regions.