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Tippling Rock Trail Head

4.6 ★★★★★ 15 Google reviews · Running trail in Sudbury, Massachusetts · Open 24 hours

Runner's snapshot

Surface: Not reported
Distance: Not reported
Shape: Not reported
Shade: Not reported
Access: Open 24 hours

Confirmed from Tippling Rock Trail Head's own listing, the park or land manager's website, and runner reviews. Blank cells mean we could not verify that fact — we would rather say "not reported" than invent one. There is no Easy / Moderate / Hard rating on this page on purpose: a one-word difficulty score tells you nothing about whether a trail suits your run. Surface, distance, shade and hours do.

Tippling Rock Trail Head — running trail in Sudbury, MA, photo 1

Tippling Rock Trail Head — running trail in Sudbury, MA, photo 2

Open 24hScenic

What runners say about Tippling Rock Trail Head

Pulled from public reviews of this trail (15 of them) — the things people bring up again and again, in their own words. Nothing here is written by us.

🏞️ beautiful scenery 4 mentions

“A very nice wooded trail leads to Tippling Rock, which provides a beautiful vista.”

Awesome local hike offering solid workout and beautiful views at the summit.

★★★★★ — Arthur , Apr 2022

Great place to take a hike. Bring the kids or your furry ones. Lots of cool sights on the way and pretty cool landscape features. It's also nice to see the Hancock and Prudential building off in the distance from the top.

★★★★★ — Adam , Aug 2021

A very nice wooded trail leads to Tippling Rock, which provides a beautiful vista.

★★★★☆ — Everett , Sep 2020

Excerpts from public Google reviews. Read all 15 reviews →

Trail conditions & character

What this trail is actually like underfoot and overhead, taken from its own listing and from reviews. Each one links to every other trail with the same character. Busy or quiet is reported as a plain fact, not a plus or a minus — a runner heading out alone at dawn often wants company on the path, and someone running intervals wants an empty one.

🏞️ Scenic views 8 mentions

“A very nice wooded trail leads to Tippling Rock, which provides a beautiful vista.”

More trails like this →

Plan your run at Tippling Rock Trail Head

The practical stuff

AccessOpen 24 hours — no gate to beat, so a 5am or a 10pm run both work
DistanceNot reported. Trail systems often quote total path mileage rather than a single loop, so measure the route you actually want before you drive out.
ShadeNot reported. Assume some of it is exposed and carry water in summer.

Hours

Monday	Open 24 hours
Tuesday	Open 24 hours
Wednesday	Open 24 hours
Thursday	Open 24 hours
Friday	Open 24 hours
Saturday	Open 24 hours
Sunday	Open 24 hours

Posted hours for the park or trailhead. Gates and parking lots often close earlier than the trail itself, and seasonal hours change — worth a check before a pre-dawn or after-dark run.

Where to find Tippling Rock Trail Head

Brimstone Ln, Sudbury, MA 01776

Get directions

Running trails near Sudbury

Other trails within easy driving distance — useful when this one is flooded, gated, or just not the run you had in mind today.

Ford's Folly

5 ★★★★★ 14 reviews

Sudbury, MA

Loop

under a mile away

Tippling Rock

4.6 ★★★★★ 87 reviews

Sudbury, MA

Natural surfaceScenicDog-friendly

Wooded trail leading to a peak with views of Boston and the surrounding area.

under a mile away

Weisblatt Conservation Land

4.9 ★★★★★ 14 reviews

Sudbury, MA

Scenic

1.0 miles away

Callahan State Park

4.5 ★★★★★ 607 reviews

Framingham, MA

ScenicDog-friendly

Trails for mountain biking, hiking, cross-country skiing, horseback riding, plus 100 acres of field.

1.6 miles away

Sudbury Conservation

4.8 ★★★★★ 4 reviews

Sudbury, MA

2.0 miles away

Callahan State Park South Entrance

4.7 ★★★★★ 132 reviews

Framingham, MA

ScenicDog-friendly

Dog-friendly park featuring hiking trails for dogs and cyclists.

2.0 miles away

All running trails in Sudbury, MA →

Nearby towns

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Listing verified July 2026 from public records, the trail's own website and runner reviews. Trail conditions change — paths flood, gates close at dusk, and shaded woods stay muddy for days after rain. Something out of date? Report a correction. Manage this trail? Send us the details — it is free.