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Hikes
United States
Massachusetts
Norfolk County

Brookline

The best walks and hikes around Brookline

4.7

(309)

5,659

hikers

12

hikes

Hiking around Brookline offers diverse landscapes, blending urban convenience with natural tranquility. The region features rolling hills, open meadows, dense wooded areas, and serene wetlands. Hikers can explore well-maintained trail systems that wind around reservoirs, through wetlands, and along river paths. This varied terrain provides options for different activity levels.

Best hiking trails in Brookline

  • The most popular hiking route is Jamaica Pond loop, a 1.8 miles (2.9 km) trail that takes 44 minutes to complete. This route offers a scenic loop around the pond.
  • Another top favourite among local hikers is Brookline Reservoir Park Trail, an easy 1.1 miles (1.7 km) path. This trail provides a relaxed walk around the reservoir.
  • Local hikers also love the Lost Pond Conservation Area, a 4.0 miles (6.5 km) trail leading through wooded areas and past a pond, often completed in about 1 hour 42 minutes.
  • Hiking around Brookline is defined by green spaces, reservoirs, and wooded areas. The network offers options for different ability levels, from leisurely strolls to longer paths.
  • The routes in Brookline are highly rated by the komoot community with an average score of 4.7 stars from over 300 reviews. More than 5000 hikers have used komoot to explore Brookline's varied terrain.

Last updated: April 26, 2026

5

hikers

#1.

Lost Pond Conservation Area

6.45km

01:42

60m

60m

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

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Easy

4

hikers

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

Easy
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1

hikers

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

Hard

36

hikers

2.87km

00:44

10m

10m

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

Easy

11

hikers

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

Easy
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Tips from the Community

AeroPetr ✈🌍
September 11, 2025, Wards Pond

The smallest of the ponds here, but no less beautiful. The dense vegetation makes you forget you're actually in the middle of a big city.

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2

0

A scenic cycle path along the river.

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AeroPetr ✈🌍
September 11, 2025, Jamaica Pond

The lake is beautifully framed by mature trees and even has a boathouse for rowers and sailors. The entire approach to the arboretum is so picturesque that you almost forget you're in the middle of a big city.

Translated by Google

2

0

great park

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0

Hans
April 4, 2025, Olmsted Park

small and nice park for a short "recovery"

1

0

In the Hüuser Gorge, the wind indicator will probably not be able to provide much data, but hikers can enjoy the many small figures on this work of art.

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1

0

A "different" art museum. Mrs. Gardner not only kept in touch with many personalities of the late 19th and early 20th centuries, she also eagerly collected art from all over the world. From parts of the architecture, to the interior design, sculptures, paintings and small accessories. The movable parts are on display, the rest are built into the palace building. This combination alone is worth a visit.

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1

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One of many parks in Boston. This one is located in the "art district" with museums and art schools.

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1

0

Frequently Asked Questions

What are the typical difficulty levels of hiking trails in Brookline?

Brookline offers a wide range of trails suitable for various abilities. The majority of routes, over 200, are classified as easy, perfect for leisurely strolls. There are also 76 moderate trails for those seeking a bit more challenge, and a few more difficult options for experienced hikers. For example, the Jamaica Pond loop — Boston is an easy, scenic walk, while the Charles River Reservation loop from Alston is considered moderate.

What natural features or landmarks can I expect to see on hikes in Brookline?

Brookline's hiking areas are rich in natural beauty and historical significance. You can explore serene water views at places like Brookline Reservoir Park and the Emerald Necklace, which features tranquil ponds and lush vegetation. Wooded areas are common in spots like Lost Pond Reservation and Hammond Pond Reservation, offering a sense of seclusion. Additionally, parks like Larz Anderson Park provide rolling hills and scenic views of the Boston skyline. You might also encounter unique rock formations at Hammond Pond Reservation or the historic Echo Bridge at Hemlock Gorge Reservation.

Are there any trails with good views in Brookline?

Yes, several spots in and around Brookline offer excellent views. Larz Anderson Park provides scenic vistas of the Boston skyline. For panoramic views of the surrounding area, Corey Hill Outlook Park is a favored spot. While hiking, you might also encounter viewpoints like Peters Hill or Bussey Hill, which are part of the nearby Arnold Arboretum, offering elevated perspectives of the landscape.

Is public transport available to reach hiking areas in Brookline?

Brookline is well-integrated with Boston's public transport system, making many parks and trailheads accessible. The MBTA (Massachusetts Bay Transportation Authority) provides bus and subway services that can take you close to popular hiking spots like Larz Anderson Park, Brookline Reservoir Park, and sections of the Emerald Necklace. It's advisable to check specific routes and schedules on the MBTA website for the most current information.

What are the parking options for trailheads in Brookline?

Many of Brookline's parks and reservations offer dedicated parking lots for visitors. For example, Larz Anderson Park has ample parking. Smaller, more urban green spaces might have street parking available nearby, though this can be limited. For larger reservations just outside Brookline, such as Cutler Park or Hammond Pond, you'll typically find designated parking areas at the main entrances. Always check local signage for any parking restrictions or fees.

When is the best time of year to go hiking in Brookline?

Brookline offers enjoyable hiking experiences throughout the year. Spring brings blooming flora and pleasant temperatures, while autumn showcases stunning fall foliage, making it a particularly popular time. Summer is great for shaded trails, and winter can offer beautiful snowy landscapes, though some paths might be icy. The well-maintained trails ensure accessibility in most seasons, but always check weather conditions before heading out.

Are there family-friendly hiking options in Brookline?

Absolutely. Brookline is ideal for family outings with many easy, accessible trails. Parks like Larz Anderson Park offer rolling hills and open meadows perfect for children to explore. Brookline Reservoir Park features a flat, one-mile loop around the water, suitable for strollers and young walkers. The Emerald Necklace also provides numerous paved and unpaved paths through green spaces, offering a gentle and engaging experience for families.

Are dogs allowed on hiking trails in Brookline?

Many of Brookline's parks and trails are dog-friendly, allowing you to enjoy hikes with your canine companion. Popular spots like Larz Anderson Park and sections of the Emerald Necklace welcome dogs, often with specific off-leash areas or designated paths. However, rules can vary by location, so it's always best to check for specific regulations regarding leashing and waste disposal at each park or reservation. For example, the Hammond and Houghton's Pond loop — Brookline is a great option for a walk with your dog.

Can I find circular hiking routes in Brookline?

Yes, Brookline features several excellent circular hiking routes. The Jamaica Pond loop — Boston is a popular 1.8-mile (2.9 km) circular trail offering scenic water views. Another great option is the Fenway Park & Black Bay Fens loop, which provides a pleasant urban circuit. Many parks, such as Brookline Reservoir Park, also feature easy loop trails perfect for a contained walk.

What do other hikers enjoy the most about hiking in Brookline?

The area is highly rated by the komoot community, with an average score of 4.7 stars from over 300 reviews. Hikers often praise the seamless blend of urban convenience with natural tranquility, the well-maintained trail systems, and the diverse landscapes. Many appreciate the accessibility of green spaces like the Emerald Necklace and the peaceful atmosphere of places like Brookline Reservoir Park, making it easy to escape into nature without leaving the city.

Are there any extensive park systems for longer walks in the area?

Yes, Brookline is home to a significant portion of the historic Emerald Necklace, designed by Frederick Law Olmsted. This park system offers miles of interconnected trails, winding paths, and lush vegetation, providing opportunities for longer walks and a harmonious blend of nature and design. It's an excellent choice for those looking for extended exploration through shaded paths, open fields, and waterfront views.

Where can I find more information about Brookline's parks and open spaces?

For additional details on Brookline's commitment to preserving its green spaces and promoting recreational opportunities, you can visit the official Brookline Parks & Open Spaces website. They provide information on various parks and initiatives. You can find more information at brooklinema.gov/Parks-Open-Spaces.

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