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United States
Massachusetts
Norfolk County

Randolph

The best walks and hikes around Randolph

4.7

(285)

1,209

hikers

141

hikes

Hiking around Randolph often involves exploring the varied landscapes of the Blue Hills Reservation. The area is characterized by a network of trails that navigate around ponds, through woodlands, and over low hills. The reservation provides a mix of relatively flat lakeside paths and more undulating routes with moderate elevation changes, making it a popular location for accessible outdoor activity near the city.

Best hiking trails around Randolph

  • The most popular hiking route is Buck Hill, Hancock Hill, and Great Blue Hill loop — Blue Hills Reservation, a 6.9 mile (11.2 km) trail that takes around 3 hours 15 minutes to complete. This route features several ascents to hills within the reservation.
  • Another top favourite among local hiking enthusiasts is Breakneck Ledge Loop – Blue Hills Reservation, a moderate 4.7 mile (7.6 km) path. The trail includes some rocky sections and elevation gain leading to viewpoints.
  • Local hiking enthusiasts also love the Ponkapoag Pond loop — Blue Hills Reservation, a 4.3 mile (6.9 km) trail leading through woodlands and along the pond's shore, often completed in about 1 hour 45 minutes.
  • Hiking around Randolph is defined by its accessible woodland trails, pond-side paths, and rolling hills. The trail network in the Blue Hills Reservation offers a variety of routes suitable for different fitness levels.
  • The routes in Randolph are highly rated by the komoot community with an average score of 4.7 stars from over 160 reviews. More than 1,100 hikers have used komoot to explore Randolph's varied terrain.

Last updated: June 24, 2026

4.7

(3)

27

hikers

#1.

Skyline Trail

23.3km

07:03

710m

770m

Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

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Hard

11

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

8

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

2

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Popular around Randolph

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Tips from the Community

Hans
December 26, 2025, Great Blue Hill Summit

A wonderfull view to Boston

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Houghton's Pond is close to the most popular trailhead and parking area within the Blue Hills Reservation. This is a popular spot, so you'll likely have to share the trail. That being said, the trails on the banks of the pond are rated as "green" trails and are pretty wide, relatively smooth, and super easy to navigate.

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Hans
January 27, 2025, Hancock Hill

If you love Boston than dicover this area with some nice views

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Nice view to Boston. There are some differnt place with awsome views

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Hans
January 15, 2025, Great Blue Hill Summit

A very great overview of Boston

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Sue
February 19, 2024, Boyce Hill

Boyce Hill is located within the stunning Blue Hills Reservation and stands at an elevation of 115 meters. While it may not be as tall as the neighboring Buck Hill peak, nor does it offer the same awe-inspiring views, it still provides some lovely vistas and is a fantastic addition to a pleasant run through this beautiful forest.

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St. Moritz is a beautiful man-made pond located on the eastern edge of Blue Hills Reservation. The pond was once a popular spot for competitive ice skaters, and hosted the annual St. Moritz Winter Carnival between 1929 and 1942, until the pond no longer froze over for such lengths of time.

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Lisa
February 9, 2024, Nahanton Hill

At 472 feet (145 m), Nahanton Hill is great for a leisurely ramble through the woods, and a pretty good view of the Boston skyline from the summit.

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Frequently Asked Questions

Are the hiking trails in Randolph suitable for families with children?

Yes, there are several family-friendly options. For a very easy and short walk, consider the Houghton's Pond loop — Blue Hills Reservation. It's a relatively flat 3 km path that's great for all ages. Many of the trails in the Blue Hills Reservation offer accessible paths through woodlands and around ponds.

Can I bring my dog on the trails around Randolph?

Dogs are generally welcome on the trails in the Blue Hills Reservation, but they must be kept on a leash. It's important to be mindful of other hikers and wildlife. Always bring water for your dog and be prepared to clean up after them to keep the trails enjoyable for everyone.

Are there any circular or loop hikes available?

Most of the popular trails in the area are loops, allowing you to start and end at the same point without retracing your steps. A great example of a relatively flat circular walk is the Ponkapoag Pond loop — Blue Hills Reservation, which takes you through woodlands and along the water's edge.

What are the parking options for the hiking trails?

There are several parking areas available for accessing the trails within the Blue Hills Reservation. Popular trailheads, such as those near Houghton's Pond and the Blue Hills Trailside Museum, have dedicated lots. These can fill up quickly, especially on weekends, so arriving early is recommended.

Are there any challenging or strenuous hikes in the Randolph area?

Yes, for those seeking a more strenuous workout with rewarding views, the Buck Hill, Hancock Hill, and Great Blue Hill loop is an excellent choice. This 11.2 km trail involves several ascents and offers some of the best panoramic views in the reservation.

How many hiking trails are there to choose from around Randolph?

There is a wide variety of options, with over 100 different hiking routes to explore in and around Randolph. These range from very easy lakeside paths to difficult hill climbs, all within the extensive network of the Blue Hills Reservation.

What do other hikers think of the trails in Randolph?

The trails are highly regarded by the komoot community, with an average rating of 4.7 out of 5 stars. Hikers often praise the well-maintained paths, the beautiful woodland scenery, and the variety of routes that cater to different fitness levels.

Are there any hikes with good scenic viewpoints?

Definitely. Many trails lead to rewarding vistas. The Breakneck Ledge Loop – Blue Hills Reservation is a moderate hike known for its rocky sections that open up to excellent viewpoints over the surrounding landscape.

What should I pack for a day hike in Randolph?

For a day hike, it's essential to wear sturdy footwear as some trails are rocky and uneven. Bring plenty of water, snacks, and a map of the Blue Hills Reservation, as cell service can be unreliable in some spots. It's also wise to pack layers of clothing, as weather can change, and insect repellent during warmer months.

Are the trails accessible by public transport?

Yes, some trailheads in the Blue Hills Reservation are accessible via public transportation. You can take the MBTA Red Line to Ashmont or Mattapan station and then connect to a bus route that stops near the reservation. Be sure to check the latest MBTA schedules to plan your trip.

Are there any easy, flat trails for a relaxed walk?

The area is perfect for relaxed walks. Of the 119 trails around Randolph, 81 are rated as easy. A great option is the Houghton's Pond and Buck Hill loop, which combines a gentle path around the pond with a small, manageable climb for a bit of variety.

Are there any waterfalls on the hiking trails?

While the Blue Hills Reservation is more known for its rolling hills, ponds, and woodlands, prominent, large waterfalls are not a key feature of the main hiking trails. The hikes focus more on forest scenery and scenic overlooks.

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