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Running trails & routes
United States
Massachusetts
Norfolk County
Brookline

Olmstead Park & Jamaica Pond loop

Moderate

3.0

(16)

81

runners

Olmstead Park & Jamaica Pond loop

00:54

8.63km

40m

Running

Embark on a refreshing jogging route around Olmstead Park and Jamaica Pond, a moderate 5.4-mile (8.6 km) loop that offers a pleasant escape. You will experience a gentle elevation gain of 126 feet (38 metres) as you follow the path, which is estimated to take about 53 minutes to complete.…

Last updated: April 23, 2026

Waypoints

A

Start point

Train Station

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1

2.70 km

Olmsted Park

Highlight • Natural

small and nice park for a short "recovery"

Tip by

2

4.57 km

Jamaica Pond

Highlight • Lake

Jamaica Pond in Boston is a lovely urban oasis! With its walking trails, serene waters, and picturesque views, it's a perfect spot to unwind, enjoy nature, or take a leisurely boat ride. Don't miss the stunning sunsets!

Tip by

B

8.63 km

End point

Train Station

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Way Types & Surfaces

Way Types

7.50 km

563 m

493 m

< 100 m

Surfaces

4.93 km

2.83 km

861 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

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Today

Wednesday 27 May

31°C

18°C

13 %

Additional weather tips

Max wind speed: 21.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How long does it take to jog the Olmstead Park & Jamaica Pond loop?

The full loop, combining Olmsted Park and Jamaica Pond, is approximately 8.6 kilometers (5.3 miles) long. For jogging, it typically takes around 50-55 minutes to complete, depending on your pace.

What is the terrain like on this jogging route?

The path around Jamaica Pond is mostly paved with some sections of cement and gravel, and is predominantly flat. Within Olmsted Park, you'll find a mix of walking paths and wooded trails, with some gentle inclines and hills. Overall, the surfaces are well-maintained and wide, suitable for jogging.

Is the Olmsted Park & Jamaica Pond loop suitable for beginners?

Yes, despite being rated as 'moderate' due to its length and some inclines in Olmsted Park, the mostly paved and well-maintained paths make it accessible for all skill levels, including beginners. You can adjust your pace or choose to do just the flatter Jamaica Pond section if you prefer an easier run.

Where can I park for the Olmsted Park & Jamaica Pond loop?

Parking is available in various spots around Jamaica Pond and Olmsted Park. Look for street parking along the perimeter roads. Public transportation is also a good option, with several bus routes serving the area, connecting to the MBTA subway system.

Is the Olmsted Park & Jamaica Pond loop dog-friendly?

Yes, the loop is dog-friendly. Dogs are generally welcome but must be kept on a leash at all times. Please remember to clean up after your pet to help keep the park beautiful for everyone.

What is the best time of year to visit this park for jogging?

The Olmsted Park & Jamaica Pond loop is beautiful year-round. Spring offers blooming flora, summer provides lush greenery, and autumn showcases vibrant fall foliage. Even in winter, the cleared paths are suitable for jogging, offering a serene, crisp experience. Weekday mornings are often less crowded.

Are there any permits or entrance fees required to access the park?

No, there are no permits or entrance fees required to enjoy the Olmsted Park & Jamaica Pond loop. It is part of Boston's historic Emerald Necklace, a public park system designed for everyone to access freely.

What kind of scenery can I expect along the route?

You'll experience picturesque and serene views throughout the loop. Highlights include the tranquil waters of Jamaica Pond, natural groves, meadows, and wooded areas within Olmsted Park. Look for historic pedestrian bridges, stone walls, and islands designed to attract wildlife, all contributing to a peaceful escape from the city.

Does the trail intersect with other well-known paths?

Yes, the route is an integral part of Boston's Emerald Necklace and intersects with several other paths. You'll find sections that are part of the Claire Saltonstall Bikeway, Walking City Trail, Boston Marathon route, and the Jamaicaway Bikepath, among others.

Is the Olmsted Park & Jamaica Pond loop wheelchair accessible?

The path around Jamaica Pond is largely paved and wide, making it generally accessible for wheelchairs and strollers. Some sections within Olmsted Park might have slight inclines or gravel surfaces, but the main loop offers a good experience for most.

Are there restrooms or water fountains available along the loop?

While there are no specific details on water fountains or restrooms directly on the trail, facilities are typically available near the boathouse at Jamaica Pond. It's always a good idea to bring your own water, especially during warmer months.

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