The Top 20 Attractions around Holbrook
There are plenty of places to see and visit around Holbrook. Whether you love hiking or cycling, Holbrook is a region where 20
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
Last updated: October 24, 2025
Chickatawbut Road
Highlight (Segment) • Viewpoint
This overlook has a great view of Boston, and is a resting point after the climbs on either side to reach the top. They're not long climbs but they will make you work for the view!
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Hancock Hill
Highlight • Summit
Although Hancock Hill is not the tallest or the most famous summit in the Blue Hills Reservation, it arguably offers some of the best view of Downtown Boston from its …
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Scenic Road by Blue Hills Reservoir
Highlight • Cycleway
You can fly downhill on the nicely surfaced road, or pedal hard against the headwind before your break at the outlook.
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Summit Staircase, Blue Hills Reservation
Highlight (Segment) • Climb
A series of deliberately placed stones form a natural-looking staircase up the trail through this small boulder field. A fun trail and great way to climb to the summit!
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Crescent Ridge Dairy Bar
Highlight • Cafe
Crescent Ridge is a local dairy with locals fields and cows. This is a great place to stop if you riding around the area, for ice cream and other refreshing …
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