Are dogs allowed on Bob's Way Loop?

Yes, dogs are allowed on Bob's Way Loop but must be kept on a leash at all times. Pack out waste and respect wildlife.

Do I need a permit to hike Bob's Way Loop?

No, Bob's Way Loop does not currently require a permit. Still check for seasonal closures or day-use fees with the managing agency before heading out.

How difficult is Bob's Way Loop?

Bob's Way Loop is rated moderate. It is 2.8 miles long with 630 feet of elevation gain. Difficulty ratings reflect a combination of distance, elevation gain, and terrain — your experience will depend on your fitness level and trail conditions.

Status unknown — verify before visiting

We don't have current condition data for this trail. Check with the land manager before you go.

See Massachusetts trail conditions

ModerateLoop

Massachusetts

Bob's Way Loop

Monterey, Massachusetts

2.8 mi

Distance

630 ft

Elev. Gain

1h 10m

Est. Time

Loop

Route Type

Moderate

Difficulty

About This Trail

Imported description

There are trails just south of Royal Pond near Route 23. The trail system was formed in honor of Bob Thieriot. The trail leads through deep woods to a secluded spot where you can rest and picnic.

Trail Conditions

Unknown

We have no current condition data for this trail. Check with the operator before you go, and submit a report below if you've been recently.

No recent condition reports. Be the first to share what you see on the trail.

Elevation Profile

Min:455 ft

Max:539 ft

192 ft

Trail Details

Route Type: Loop
Surface: Dirt

Official sources & verification

We don't have curated agency sources for this trail in our cache yet. Outdoors is not the permitting authority — confirm conditions, permits, and access with the managing agency before you go. If you know who manages this trail, please tell us.

Reviews

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Legacy import — verify before navigating

Path geometry came from our pre-launch legacy database. Routes have not yet been re-verified against the operator and may differ from the actual trail.