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Rocky Woods

Details unconfirmedPreserve · Holliston, MA
Right now

A roughly 162-acre conservation parcel at the corner where Holliston, Hopkinton and Milford meet, centered on the College Rock trailhead with a climbable rock face, a boardwalk over a swampy pond and stone walls threading through the woods. This is a distinct, locally known Rocky Woods and not the famous 491-acre Trustees of Reservations property of the same name, which is centered in Medfield roughly 15 miles east.

What to expect

Parking
Free lot free · unconfirmed
Trails
Trails moderate, fine for joggers and… · natural, with a wooden bridge crossing…
Entry fee
Free
Dogs
Holliston's Animal Control bylaw requires owners to keep their dog from running at large, in effect a townwide leash rule enforced by the Animal Control Officer. Posted signs at the site take precedence.
Hours
No posted opening or closing time. Signs at the entrance win if they differ. That's the town default unless posted otherwise.
Managed by
Holliston Conservation Commission 508-429-0607 · Website

What's here

On site

Info kiosk
information kiosk at College Rock shows conservation land maps and rock-climbing routes

Common questions

Is this the famous Rocky Woods with the pond and boathouse?
No, that larger Trustees of Reservations property is in Medfield; this Holliston-area Rocky Woods is a smaller, separately managed parcel at the Hopkinton and Milford line.
Where do I park at Rocky Woods?
Free lot (free).
Are there trails at Rocky Woods?
Yes. moderate, fine for joggers and mountain bikers but not… difficulty. Surface: natural, with a wooden bridge crossing a swamp and….
Is there an entry fee at Rocky Woods?
No, entry is free.
Can I bring my dog to Rocky Woods?
Holliston's Animal Control bylaw requires owners to keep their dog from running at large, in effect a townwide leash rule enforced by the Animal Control Officer. Posted signs at the site take precedence.
What rules should I know at Rocky Woods?
Trail names and map markings do not always match what is posted on the ground, so out-and-back routes are the safer plan for first-time visitors.

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Parks (8) · Ponds (3) · Lakes (1) · Playgrounds (1)

BetaSome details here are unconfirmed (hours, accessibility). Details are sourced from public agency data and can change through the season. Confirm locally before you go. Sourced 2026-07-22. Official source. Updated 2026-09-13.