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Suffolk County

Oakdale

The best walks and hikes around Oakdale

5.0

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57

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24

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Hiking around Oakdale, New York, is characterized by its predominantly flat terrain, offering routes through preserves and state parks on Long Island. The region features trails that follow riverbanks, wind through woodlands, and explore coastal areas. Paths include a mix of paved and unpaved surfaces with minimal elevation change, making them suitable for various ability levels.

Best hiking trails around Oakdale

  • The most popular hiking route is Long Island Greenbelt Trail South, a 7.0 miles (11.4 km) trail that takes 2 hours 52 minutes to complete. This route offers a moderate path through varied landscapes.
  • Another top favourite among local hikers is Long Island Greenbelt Trail Loop, a moderate 6.3 miles (10.2 km) path. This trail provides a scenic loop through the area's natural settings.
  • Local hikers also love the Heckscher State Park Bike Path, a 3.6 miles (5.8 km) trail leading through Heckscher State Park, often completed in about 1 hour 27 minutes.
  • Hiking around Oakdale is defined by woodland paths, river trails, and coastal park routes. The network of trails provides options for different ability levels, from short, easy walks to longer moderate hikes.
  • The routes in Oakdale are highly rated by the komoot community with an average score of 4.2 stars from 5 reviews. More than 50 hikers have used komoot to explore Oakdale's varied terrain.

Last updated: October 2, 2026

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#1.

Bayard Cutting Arboretum Loop

3.57km

00:55

10m

10m

The Bayard Cutting Arboretum Loop offers a serene and easy hike, guiding you through a living museum of trees. You'll wander past ancient oak trees and impressive conifers, with the trail eventually leading you to the tranquil Connetquot River, where bald cypress trees stand with their distinctive "knees." This 2.2-mile (3.6 km) route, with a minimal 38 feet (12 metres) of elevation gain, is perfect for a leisurely 54-minute stroll, making it ideal for families and those seeking a quiet botanical experience.

Planning your visit is straightforward, with ample parking usually available, though an early start is always recommended on busy days. The arboretum is particularly stunning in late summer and early fall when the Dahlia Garden is in full bloom, or during autumn for its vibrant foliage. You can also find a cafƩ in the historic Manor House, perfect for a refreshment after your walk.

What makes this trail truly special is its unique blend of curated botanical collections and historical significance, influenced by Frederick Law Olmsted. It's an "oasis of beauty and quiet" on Long Island, offering educational placards to identify various tree species and even a farm with chickens, adding to its distinct charm and appeal for all ages.

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If you're looking for a genuinely easy hike with plenty of visual interest, the Heckscher State Park Bike Path delivers. This 3.6-mile (5.8 km) route offers a pleasant journey through diverse scenery, from shaded woodlands to open coastal stretches with continuous views of the Great South Bay. With only 16 feet (5 metres) of elevation gain, it's a flat and well-maintained path, making it ideal for a leisurely stroll or a family outing.

Planning your visit to Heckscher State Park is straightforward, as the park provides numerous amenities like picnic areas, playgrounds, and restrooms. While specific parking information isn't detailed, the state park is large, suggesting ample parking is available. The trail is accessible for all skill levels and can be enjoyed throughout the year, though coastal sections might be windy.

This trail is notable for being part of the extensive 1,600-acre Heckscher State Park, and it also serves as the southern trailhead for the much longer 32-mile Long Island Greenbelt Trail. The park's rich natural environment means you'll encounter diverse ecosystems, from forests to marshland, and have opportunities to spot wildlife like white-tailed deer and over 280 species of birds.

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The Long Island Greenbelt Trail South offers a truly varied hiking experience, guiding you through lush forests, past picturesque river views, and along the edge of the Great South Bay. You'll traverse soft, sandy sections, boardwalks, and natural soil paths, with the terrain shifting from flat pine plains to gently rolling hills, especially as you pass through areas like Heckscher State Park. Keep an eye out for local wildlife, including deer and a variety of bird species, as you immerse yourself in this diverse natural setting.

This moderate 7.1-mile (11.4 km) hike, with a minimal 49 feet (15 metres) of elevation gain, typically takes around 2 hours and 51 minutes to complete. While generally accessible, some parts require good fitness. The trail is marked with white blazes, but be prepared for potential sections that might lead through suburban streets, requiring careful navigation. Fall is an especially rewarding time to visit, as the foliage bursts into vibrant colors.

Part of the larger 32-mile Long Island Greenbelt Trail, this southern section is a designated National Recreation Trail that connects the Great South Bay to the Long Island Sound. It provides access to significant state parks like Connetquot River State Park Preserve and Heckscher State Park, and closely follows the courses of the Connetquot and Nissequogue rivers. The trail's rich biodiversity offers excellent opportunities to observe a wide array of plant and animal species.

Moderate

The Connetquot River State Park Preserve offers a delightful, easy hiking experience, perfect for a quick nature fix on Long Island. This 2.9-mile (4.7 km) loop takes you through varied terrain, from sandy pine barrens to wetlands and dense woodlands, all centered around the picturesque Connetquot River. With only 18 feet (6 metres) of elevation gain, it's a gentle stroll that can be completed in about 1 hour and 10 minutes, making it one of the best easy hiking trails in the area.

Planning your visit is straightforward; the park is generally accessible, though it's always wise to check for any specific permit requirements or seasonal hours on their official site. Parking is usually available, but arriving earlier in the day can help you secure a spot and enjoy the tranquility before it gets too busy. This trail is particularly family-friendly, offering a relaxed pace for all ages.

What truly sets this preserve apart is its rich biodiversity and historical significance. As you hike, you'll have opportunities for wildlife spotting, with deer, waterfowl, and even river otters frequently seen. The route also passes by landmarks like the historic Nicoll Grist Mill, providing a glimpse into the past amidst the natural beauty. It's a hidden gem for those seeking a peaceful escape and natural features on Long Island.

Easy

5.0

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3

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This Long Island Greenbelt Trail Loop offers a delightful journey through varied terrain, showcasing the region's natural beauty without demanding a huge effort. You'll wander through peaceful wooded areas and encounter gently rolling hills, with the trail occasionally following the course of the Connetquot River. Keep an eye out for Bunce's Bridge, a charming landmark that provides a pleasant crossing over the water, adding a touch of character to your hike.

Planning your visit to this moderate 6.3-mile (10.2 km) loop, which typically takes around 2 hours and 34 minutes, is straightforward. The trail has a minimal elevation gain of 38 feet (12 metres), making it accessible for many. While the route is generally well-marked in its wooded sections, it's wise to stay attentive to trail markers, as the wider Greenbelt system can sometimes be tricky to navigate near roads. Check for any specific park entry requirements or hours before heading out.

This particular loop is a fantastic way to experience a segment of the larger 32-mile Long Island Greenbelt Trail, which holds the distinction of being a National Recreation Trail. It provides a unique opportunity to see a cross-section of Long Island's landscapes, from diverse ecosystems along river courses to glimpses of pine plains. The trail's connectivity to various state parks, like Connetquot River State Park Preserve, highlights its importance in preserving and showcasing the island's natural heritage.

Moderate
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Tips from the Community

oliviakellis
May 26, 2024, Heckscher State Park

Spanning 1,600 acres on Long Island's south shore, Heckscher State Park is an outdoor haven. Shady picnic groves host family gatherings, while open fields beckon sports enthusiasts for soccer, cricket, and lacrosse. Nature lovers explore 4 miles of trails, spotting deer and birds against the backdrop of the Great South Bay and Fire Island. The bay lures visitors for swimming, boating, and water sports. Newly built waterfront cottages offer cozy accommodations with spectacular views, complete with living areas, kitchens, and screened porches.

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Connetquot River State Park Preserve is a 3,473-acre refuge of sandy pine barrens, wetlands, ponds, and woodlands. Visitors can find over 200 bird species and 300 plant species, along with other mammals, reptiles, amphibians, butterflies, and moths that once lived all over Long Island. This area was created as New York's first "State Park Preserve," and remains a protected area open to the public today.

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This nearly 3,500-acre refuge of sandy pine barrens, wetlands, ponds and woodlands is nestled in central Long Island along the pristine, spring-fed Connetquot River. A wilderness surrounded by suburbs, the preserve provides excellent opportunities to see more than 200 bird and 300 plant species, as well as several mammal, reptile, amphibian, butterfly and moth species that once flourished throughout Long Island.

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This is a nice river crossing. What a pleasant spot!

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The mill was recently renovated and is open for tours. It sits on the Main Pond and was used to mill local grains, wheat and corn back in the 1700's.

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Frequently Asked Questions

Are there any easy, family-friendly hikes in Oakdale?

Yes, the area has several easy trails perfect for a family outing. A great option is the Sunken Forest loop — Sailor's Haven, a short 1.6-mile (2.6 km) walk through a unique maritime forest that can be completed in about 40 minutes. Another good choice is the Nicoll Grist Mill – Fish Hatchery loop from East Islip, which is a gentle path suitable for all skill levels.

Can I bring my dog on the hiking trails around Oakdale?

Dog policies vary by park. In Connetquot River State Park Preserve, pets are generally not permitted on the trails to protect the wildlife. However, Heckscher State Park typically allows dogs on leashes in specific areas. It's always best to check the official park regulations for the most current information before you go.

Are there any challenging hikes or trails with significant elevation?

The terrain around Oakdale is predominantly flat, characteristic of Long Island's coastal plain. As a result, you won't find any difficult hikes with significant elevation gain. The trails are mostly rated as easy or moderate, focusing on pleasant walks through woodlands and along the coast rather than strenuous climbs.

What do other hikers think of the trails in Oakdale?

The trails around Oakdale are well-regarded by the komoot community, earning an average rating of 4.2 stars. Hikers often praise the peaceful woodland paths within Connetquot River State Park Preserve and the scenic coastal views at Heckscher State Park.

What is the best time of year to hike in Oakdale?

You can hike in Oakdale year-round, but spring and fall offer the most pleasant experience with comfortable temperatures and beautiful scenery. Summer is also popular, especially for coastal trails, though it can be hot and humid. Winter hiking is possible, offering a quieter experience, but be prepared for colder weather.

Are the trails suitable for trail running?

Many of the trails are well-suited for running. The terrain is mostly flat with a mix of paved and unpaved paths. Routes like the Heckscher State Park loop via Long Island Greenbelt Trail offer a longer, continuous path that is popular with local runners.

Do I need to pay to hike in the state parks near Oakdale?

Yes, state parks like Connetquot River State Park Preserve and Heckscher State Park typically charge a vehicle entrance fee, especially during peak season (spring through fall). The fees help maintain the park facilities and trails. It's a good idea to check the official NY State Parks website for current rates and hours.

What kind of scenery can I expect on the trails?

The scenery is defined by Long Island's natural landscapes. You'll hike through serene woodlands with native trees, follow paths along the banks of the Connetquot River, and explore trails that offer expansive views of the Great South Bay from coastal parks.

Are there any circular walks available?

Yes, many of the best routes are loops, allowing you to start and end in the same place without retracing your steps. The Green & Long Island Greenbelt Trail Loop is a great example of a moderate circular hike within Connetquot River State Park Preserve.

How many hiking trails are there around Oakdale?

There are over 15 hiking routes to explore around Oakdale. The network includes everything from short, easy walks under an hour to more moderate hikes that take several hours to complete, offering plenty of options for a day outdoors.

Can I get to the trailheads using public transport?

Accessing the trailheads via public transport can be challenging. The major parks, like Connetquot and Heckscher, are best reached by car. The Oakdale and Great River stations on the Long Island Rail Road are nearby, but you would likely need a taxi or rideshare for the final few miles to the park entrances.

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