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Greater Boston Hikes — stop photo 1
Greater Boston Hikes — stop photo 2
Greater Boston Hikes — stop photo 3
Greater Boston Hikes — stop photo 4

Challenge

Greater Boston Hikes

Boston, MA

Greater Boston Hikes — stop photo 1
Greater Boston Hikes — stop photo 2
Greater Boston Hikes — stop photo 3
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About this challenge

The Greater Boston Hikes Slug is a 25-mile hiking challenge that takes you through the city’s diverse neighborhoods and natural landscapes, offering a mix of urban exploration and outdoor adventure within Boston, MA.

Quick facts

Checkpoints
6
Distance
25 miles
Avg Completion
1-2 years
Best Season
Summer, Spring, Fall
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Rewyld app

by Rewyld

A mindful companion app for your hikes.

Rewyld guides a five-minute walking meditation as you hike, so you slow down and stay present, then it steps out of the way. Take it on any trail.

Try Rewyld freeiOS & Android

Featured checkpoints

Purgatory Chasm

Purgatory Chasm

Sutton, MA

1.5 milesEasy
Mount Monadnock

Mount Monadnock

Jaffrey, NH

4.5 milesModerate
Blue Hills Skyline Trail

Blue Hills Skyline Trail

Blue Hills Reservation, MA

7.5 milesModerate
Middlesex Fells Skyline Trail

Middlesex Fells Skyline Trail

Middlesex Fells Reservation, MA

7 milesModerate
Mount Wachusett

Mount Wachusett

Princeton, MA

6 milesModerate
World’s End Trail

World’s End Trail

Hingham, MA

4.5 milesEasy

Greater Boston Hikes: common questions

How long is Greater Boston Hikes?

Greater Boston Hikes covers 25 miles in total.

How long does Greater Boston Hikes take to complete?

Most people complete Greater Boston Hikes in about 1-2 years.

When is the best time to do Greater Boston Hikes?

The best season for Greater Boston Hikes is Summer, Spring, Fall.

How many checkpoints does Greater Boston Hikes have?

Greater Boston Hikes has 6 checkpoints to log on the way to finishing it.