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Hiking trails & Routes
United States
Massachusetts
Suffolk County
Boston

Walking City Trail: Section 1

Moderate

4.8

(8423)

15,554

hikers

Walking City Trail: Section 1

03:28

13.4km

70m

Hiking

Embark on the Walking City Trail: Section 1, a moderate hiking route that guides you through Boston's green spaces and urban landscapes. This section covers 8.4 miles (13.4 km) and involves a total elevation gain of 245 feet (75 metres), offering a diverse experience from dense woodlands along the Neponset River to expansive urban forests. You will encounter varied terrain, including sidewalks, dirt paths, and rocky sections, with highlights like Pretty Pond providing scenic breaks.

Planning your visit is straightforward, as the trail is easily accessible via public transit, allowing you to explore Boston's neighborhoods without needing a car. The estimated duration for completing this section is around 3 hours and 27 minutes, so plan your start time accordingly. While there are no specific permits or seasonal closures to worry about, be prepared for the varied surfaces and some stairs or boardwalks along the way.

This trail offers a unique perspective on Boston, blending natural beauty with the city's built environment. The route culminates with a rewarding panoramic view of the Downtown Boston skyline from the city's tallest hill. Following this, you will descend into a charming "fairy village," adding a whimsical touch to your urban hiking adventure.

Last updated: April 23, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Waypoints

A

Start point

Bus stop

Get Directions

1

2.22 km

Harvest River Bridge

Highlight • Bridge

This bridge that offers a beautiful view of the Neponset River is extremely unusual. Structurally, it can be classified as an arched bridge. It has only four or five hangers connecting the arch structure to the apron.

Tip by

2

2.84 km

Part of the Neponset river bike route. Crowded with families on Sunday!

Tip by

3

2.85 km

Neponset River Reservation

Highlight • River

Neponset River Reservation is a nature lover's paradise in the Boston area. With scenic trails, wetlands, and riverfront views, this hidden gem offers a peaceful retreat from the bustling city.

Tip by

3.47 km

Church of the Holy Spirit

Place Of Worship

5

7.37 km

Weider Park

Highlight • Rest Area

Weider Park is a small DCR-owned park on the border of Roslindale and Hyde Park. There’s 2 tennis courts which are reasonably well kept and a small playground but nothing else - no water, no bins, no toilet. It does back onto the Urban Wilds or Sherrin Woods which are beautiful. Your shouldn’t ride your bike there, although there is an unofficial bikeable trail along the railway track (behind the sad chain gate) from the north, or behind the rocks from the south.

Tip by

6

8.18 km

Sherrin Woods Urban Wild

Highlight • Forest

This is the 2nd largest urban wild site, located between the MBTA commuter rail tracks and Austin Street, just north of West Street. The northern half of the site is dominated by a rocky outcrop, known as Pine Rock, and forest comprised primarily of mature oaks, hickory, cherry, birch, and hemlock. The southern portion of the site is mostly filled-in stream channels and wetlands, which have gradually developed into a dense, weedy thicket of non-native, invasive shrubs and small trees. There are trails traversing the northern portion of the site. Along the eastern edge of the site is a right-of-way for the Stony Brook Conduit, replacing the now buried Stony Brook. Because of its size and accessibility, Sherrin Street Woods offers local residents many opportunities for passive recreation and natural history education, as well as significant aesthetic values. This large site helps break up the uniformity of many, small single-family house lots, and provides an appealing semi-rural feel to the neighborhood.

Tip by

7

11.9 km

Boundary I Urban Wild

Highlight • Forest

The DCR has acquired the majority of this site and has incorporated it into the Stony Brook Reservation. However, one City-owned parcel adjacent to the George Wright Golf Course and High Point Village contains a healthy cattail marsh surrounded by upland forest.

The wetland is believed to be a habitat for the rare spotted turtle.

A mixed deciduous forest, predominantly composed of oaks and birch, covers the upland areas while the lowland area hosts traditional wetland species such as sweet pepperbush, highbush blueberry, lowbush blueberry, and witchhazel. Teaberry, sweet fern, and ferns are common groundcover.

Ecologically and topographically, the parcel is contiguous with the reservation. In fact, the only feature marking the site is the fence and rock wall that divides the parcel from the golf course

Tip by

8

13.3 km

Pretty Pond

Highlight • Lake

I ran this as a loop starting on Churchill st . Park has quite a trail network

Tip by

B

13.4 km

End point

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Way Types & Surfaces

Way Types

6.91 km

3.40 km

2.84 km

270 m

< 100 m

Surfaces

5.19 km

3.09 km

2.10 km

1.43 km

1.31 km

307 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

Thursday 16 July

32°C

18°C

32 %

Additional weather tips

Max wind speed: 26.0 km/h

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Frequently Asked Questions

How long does it typically take to hike Walking City Trail: Section 1?

This section is approximately 8.3 miles (13.4 km) long and generally takes around 3 hours and 27 minutes to complete. However, your actual hiking time may vary depending on your pace and how often you stop to enjoy the scenery.

What is the difficulty level of this trail section?

Walking City Trail: Section 1 is considered to have a moderate difficulty. While some shorter loops within it are rated as 'easy', the varied terrain, including rocky and rooty paths, stairs, and boardwalks, presents a moderate challenge within an urban setting. It's suitable for most hikers with a reasonable level of fitness.

Where does Walking City Trail: Section 1 start and end, and where can I park?

The trail kicks off at the Harvest River Bridge. It concludes with a rewarding view of the Downtown Boston skyline, followed by a descent to a 'fairy village'. Parking can often be found near the Neponset River Reservation, though specific trailhead parking can be limited. Consider public transport for easier access.

What kind of terrain can I expect on this section of the trail?

The terrain is quite diverse, offering a true urban hiking experience. You'll encounter a mix of sidewalks, dirt paths, gravel paths, and even some rocky and rooty sections. The route also includes stairs, boardwalk segments, and bridges, showcasing Boston's varied green spaces and built environments.

What are some notable sights or highlights along the route?

This section offers a rich visual experience. You'll trace the Neponset River through dense woodlands, venture into an expansive urban forest, and pass by Pretty Pond. Highlights include crossing the Harvest River Bridge and the Bike bridge over the Neponset River. The trail culminates with a panoramic view of the Downtown Boston skyline and a charming 'fairy village'.

Is Walking City Trail: Section 1 dog-friendly?

Yes, this section of the trail is generally dog-friendly. However, as parts of the trail pass through areas like the Neponset River Reservation and other urban wilds, it's essential to keep your dog on a leash and follow all local regulations regarding pet waste and control. Always check for specific signage along the route.

Do I need a permit or pay an entrance fee for this trail?

No, you do not need a permit, and there are no entrance fees to hike Walking City Trail: Section 1. It is part of a public urban trail system designed for accessibility and enjoyment by all.

What is the best time of year to hike this section?

Spring and fall offer the most pleasant hiking conditions with mild temperatures and beautiful foliage. Summer can be enjoyable, but be prepared for warmer weather. While possible in winter, some sections might be icy or muddy, requiring appropriate footwear and caution. The varied urban and natural scenery makes it a worthwhile hike in any season.

How can I access the trailhead using public transport?

The Walking City Trail is designed to be public transit-accessible, allowing you to explore Boston's green spaces without a car. Specific bus or subway stops near the starting point at Harvest River Bridge can be found by checking the MBTA (Massachusetts Bay Transportation Authority) website for current routes and schedules to the Neponset River area. This makes it easy to reach the trail and explore Boston's neighborhoods.

Are there amenities like restrooms or places to eat nearby?

As an urban trail, you'll find various amenities along or near the route, especially when passing through residential areas. Weider Park is one highlight that may offer facilities. For restrooms, cafes, and restaurants, it's best to plan ahead and check maps for options in the neighborhoods the trail traverses, particularly towards the end of the section.

Does this trail section intersect with other well-known paths?

Yes, this section of the Walking City Trail integrates with several other paths. The route also passes through sections of the Neponset River Greenway and the Claire Saltonstall Bikeway, offering connections to a broader network of trails within the city.

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