The best walks and hikes around Berkshire Lakes
4.5
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Hiking around Berkshire Lakes provides access to a network of trails through the coastal and urban landscapes of Naples, Florida. The region is characterized by flat terrain, with routes following paved greenways, city paths, and sandy beaches. These trails offer walks along the Gordon River and the Gulf of Mexico coastline.
Best hiking trails around Berkshire Lakes
- The most popular hiking route is Naples Beach and Gordon River Greenway loop — Naples, a 8.6 mile (13.8 km) trail that takes around 3 hours 30 minutes to complete. This route combines sections along the river with paths near the beach.
- Another top favourite among local hiking enthusiasts is Naples Beach via 5th Avenue (Old Naples) — Naples, a moderate 5.9 mile (9.5 km) path. The trail explores the Old Naples area before leading to the coastline.
- Local hiking enthusiasts also love the Naples Botanical Garden loop — Naples, a 1.8 mile (2.9 km) trail leading through cultivated gardens, often completed in about 45 minutes.
- Hiking around Berkshire Lakes is defined by paved urban greenways, sandy coastal paths, and trails through city parks. The network provides options for different ability levels, with most routes being easy or moderate.
- The routes in Berkshire Lakes are highly rated by the komoot community with an average score of 4.9 stars from a number of reviews. More than 200 hikers have used komoot to explore Berkshire Lakes's varied terrain.
Last updated: June 29, 2026
5.0
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8.11km
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Explore the 5.0 miles (8.1 km) Gordon River Greenway, a moderate hike through diverse ecosystems and urban nature in Naples, Florida.
4.5
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9.53km
02:23
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Hike 5.9 miles along Naples Beach via 5th Avenue (Old Naples), combining urban charm with coastal beauty and Gulf of Mexico views.
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13
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2.55km
00:38
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An easy 1.6-mile (2.5 km) hiking loop around Lake Avalon in Sugden Regional Park, perfect for a quick, flat walk with lake views.
1.54km
00:23
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Explore the easy 1.0-mile Freedom Park loop in Naples, Florida, featuring diverse terrain, boardwalks, and wildlife around ponds and lakes.
26
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Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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Popular around Berkshire Lakes
Tips from the Community
perfect road feeling with a touch of luxury
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beautifully designed little alley
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the city and private owners spend a lot of money on the appearance
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great little place in the hustle and bustle of tourists
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In addition to the beautiful architecture and the weather, there is also live music
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A visit in the evening is recommended - this sunset is fantastically beautiful
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The Naples Beach stretches for nearly nine miles along the west coast of Florida. There are numerous public access points at the ends of most roads in downtown Naples. All of Naples Beach has pure white sand and crystal clear, clean water, making it a must-visit. There are public restrooms and showers too. Since Naples is on the west coast, Naples Beach is a must-visit at sunset - they are truly magnificent!
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The historic Naples Fishing Pier and adjacent stretches of beach are the heart of the long Naples Beach. The iconic pier stretches out for 1,000 feet into the ocean, providing you with unparalleled views of the beautiful coastline. The Naples Pier beach, like the rest of Naples Beach, is beautiful with white sand and clear, blue water.
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Frequently Asked Questions
Are the hiking trails in the Berkshires suitable for families with children?
Yes, the Berkshires offer many family-friendly options. A great choice is the Naples Botanical Garden loop, which is a short and easy walk. For a paved, multi-use path that's perfect for strollers and little legs, the Ashuwillticook Rail Trail is a highly-regarded local favorite.
Can I bring my dog on the hiking trails?
Many trails in the region are dog-friendly, but policies can vary, especially in state parks and wildlife sanctuaries. For example, places like Pittsfield State Forest and Beartown State Forest generally welcome leashed dogs on their trails. Always check the specific regulations for the park you plan to visit before you go.
Are there any circular or loop hikes available?
Absolutely. The region has several excellent loop trails that bring you back to your starting point. For a walk that combines city and coastal scenery, consider the Downtown Naples and Naples Beach loop. Another popular option is the easy 1.5-mile Pond Trail loop around Benedict Pond in Beartown State Forest.
What are some popular places to go hiking in the Berkshires?
The Berkshires are full of well-loved hiking destinations. October Mountain State Forest is the state's largest, offering numerous trails including a section of the Appalachian Trail. For fantastic views, Olivia's Overlook at Yokun Ridge Reserve is a popular spot with well-marked trails. Pittsfield State Forest is another great choice, known for its extensive trail network and a pond for swimming.
Where can I find hikes with good scenic viewpoints?
For stunning panoramic views, Olivia's Overlook at Yokun Ridge Reserve is a top-rated local favorite, especially during the fall. Another excellent choice is Monument Mountain, which rewards hikers with beautiful vistas of the Housatonic River Valley.
What is the best time of year to hike in the Berkshires?
Hiking in the Berkshires is enjoyable year-round, but autumn is particularly spectacular due to the vibrant fall foliage, making it a very popular season. Summer offers lush green forests and warm weather, while spring brings wildflowers. Winter is great for snowshoeing and cross-country skiing on many of the same trails.
Are there any trails that go near lakes or rivers?
Yes, many trails feature water views. The Gordon River Greenway offers a pleasant walk along the river. Beartown State Forest features a lovely trail around Benedict Pond, and many other state forests in the area have trails that lead to or circle ponds and lakes.
How difficult are the hiking trails in this region?
The trails are quite varied, catering to all skill levels. You'll find everything from flat, paved rail trails to challenging ascents up mountains like Mount Greylock. The majority of the routes in our collection are rated as easy or moderate, such as the 20 easy and 10 moderate trails available.
Are there any hiking trails with waterfalls?
Yes, you can find some beautiful waterfalls in the Berkshires. A well-known short hike is the trail at Stevens Glen, which leads to a dramatic cascade in a rocky ravine. You can also find smaller waterfalls and cascades within larger parks like Pittsfield State Forest, especially after heavy rain.
What do other hikers think of the trails in the Berkshires?
The area is highly rated by the komoot community, with an average score of 4.9 stars. Reviewers often praise the well-maintained trails, the beautiful forest scenery, and the variety of hikes available, from peaceful lakeside walks to rewarding mountain summits.
How should I prepare for a day hike in the Berkshires?
Wear sturdy, comfortable footwear. Weather can change quickly in the mountains, so it's wise to dress in layers and pack a waterproof jacket. Bring plenty of water and some snacks. It's also a good idea to have a map of the area, either on your phone with the komoot app or a physical copy, as cell service can be unreliable in some parts of the forests.
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