Kent itinerary scene

Weekend itinerary

A Kent weekend from Kent Falls to Bulls Bridge

Arrive in the village Friday, give Saturday morning to Kent Falls or a prepared ridge hike, then return for books, galleries, and a reserved dinner. Use Sunday for Bulls Bridge and the Housatonic before departure.

By Cal Mercer — a Second Star Guide itinerary

Kent’s weekend sequence moves from the waterfall or ridge to Main Street, then south to Bulls Bridge.

Best length

2 nights

Two nights cover one substantial outdoor outing, the village while shops are open, and a separate Housatonic stop without repeating the same circuit.

Stay

The Kent Collection The Firefly Inn

A renovated and refurnished former B&B on North Main Street, with rooms and suites for up to 18 guests and Kent…

Main activity

Kent Falls State Park

Kent Falls has a paved base approach and short, steep Steps Trail; longer ridge hikes require current maps and more daylight.

Route mix

Waterfall, village, and river

Choose Kent Falls or a longer ridge hike for Saturday morning; the routes require different mileage, footing, and daylight.

Contextual ink watercolor of stone steps beside an autumn cascade
Cascade stairs and autumn woods frame the shorter waterfall choice.
Contextual ink watercolor of a hiker on a rocky hardwood ridge
Rocky ridge terrain calls for current maps, daylight, and secure footing.
Contextual ink watercolor of a covered timber bridge above an autumn river
The Sunday river stop is separate from the walkable village center.

Friday

Arrive in Kent village

Check in, walk Main Street while doors are still open, and keep the first dinner close to the room.

4:00 PM

Saturday

Waterfall stairs or ridge terrain, then village art

Use the Steps Trail for a short cascade outing, or choose the AT or Cobble Mountain only after checking the current map and Macedonia Brook reroute.

2:30 p.m.

Afternoon

Change shoes and walk the village

Visit House of Books, Kent Barns, and current gallery openings during their daytime hours before dinner.

Sunday

Bulls Bridge and the Housatonic

Use daylight for the covered bridge and river, then leave by the route that fits the next destination.