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New York
Suffolk County

Smithtown

The best road cycling routes around Smithtown

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(7)

243

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58

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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.

Best road cycling routes around Smithtown

  • The most popular road cycling route is Mount Sinai Harbor Loop, a 48.9 miles (78.6 km) trail that takes 3 hours 23 minutes to complete. This moderate route offers scenic harbor views and includes 1581 feet (482 meters) of elevation gain.
  • Another top favourite among local road cyclists is Cordwood Park – Avalon Nature Preserve loop from Smithtown, a moderate 29.4 miles (47.3 km) path. This route leads through varied terrain, including sections near the Avalon Nature Preserve, offering glimpses of woodlands and wetlands.
  • Local road cyclists also love the Old Field Point Light – Cordwood Park loop from Smithtown, a 47.0 miles (75.6 km) trail leading through coastal areas and parklands, often completed in about 3 hours 33 minutes.
  • Road cycling around Smithtown is defined by rolling hills, river systems, and extensive parklands. The network offers options for different ability levels, from moderate to more challenging rides.
  • The routes in Smithtown are highly rated by the komoot community with an average score of 3.5 stars from over 6 reviews. More than 270 road cyclists have used komoot to explore Smithtown's varied terrain.

Last updated: October 30, 2026

7

riders

#1.

Mount Sinai Harbor Loop

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.
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Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Smithtown

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Tips from the Community

Lisa
February 17, 2024, Short Beach

This beach is a nice spot for swimming, with restrooms, playground equipment, campsites and a refreshment stand. The water usually passes cleanliness standards.

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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.

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Alex
January 31, 2024, Sandy Beach

This sandy beach is a perfect spot to take a break off of the bike and enjoy the views. If the weather and sea state are good you could go for a cool off on a summers day.

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Alex
January 31, 2024, Asharoken Beach

Cyclists are drawn to the enchanting allure of Asharoken Beach, NY. This scenic coastal retreat offers a serene escape with its soft sands, rhythmic waves, and panoramic views. Cyclists find respite in the tranquil atmosphere, where the combination of natural beauty and peaceful surroundings makes it an idyllic stop along their journey.

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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.

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Christopher
August 18, 2023, Cordwood Park

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.

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make sure you hook a left when harbor Hill splits

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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.

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Frequently Asked Questions

How many road cycling routes are available in Smithtown?

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.

What kind of terrain can I expect on road cycling routes in Smithtown?

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.

Are there any circular road cycling routes in Smithtown?

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.

What natural features or landmarks can I see along the road cycling routes?

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.

What is the best time of year for road cycling in Smithtown?

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.

Are there any family-friendly road cycling options in Smithtown?

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.

What do other road cyclists enjoy most about cycling in Smithtown?

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.

Are there any cafes or places to stop for refreshments near the cycling routes?

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.

Where can I find parking for road cycling routes in Smithtown?

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.

Can I access Smithtown's cycling routes using public transport?

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.

Are there any advanced or more challenging road cycling routes in Smithtown?

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.

What are some notable viewpoints along the road cycling routes?

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.

Most popular routes around Smithtown

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