Directions from Pittsburgh, Pennsylvania to Lenox, Massachusetts

UpTake Roadtrip Beta

We've selected a few points along the way for you to stop. We are trying to surface things you may not find elsewhere, but if we make some poor choices, please understand. Your feedback is appreciated.

Town Tavern

Bars – Duryea, Pennsylvania

3.5

1 source

Average Rating	3.5 out of 5	overall rating
CitySearch	3.5	overall rating

Berkshire East Ski Area

Ski Resorts – Charlemont, Massachusetts

on my last trip to berksire east my time was great there chair lifts where a little slow in the evening but... More on SkiSite

4.0

1 review
1 source

Average Rating	4.0 out of 5	1 review 1 source
CitySearch	4.0	1+ reviews

More Reviews

If you've ever been to Magic in Vermont, it's similar minus the overall quality of the hill.. More on SkiResortGuide.com
Truely a quaint ski area. Located along route 12 (the mohak trail) right behind the quiet village of Charle... More on CitySearch

American Legion

Things To Do – Rensselaer, New York

The Inner Wall

Things To Do – New Paltz, New York

Indoor rock climbing gym. More on iloveny.com

Wolf Run Rail Trail

Things To Do – Falls Creek, Pennsylvania

You can tell this is a new trail. The northern end is shale that has been dozed and is very rough. Fortunately it is only a short distance before you run out of the shale but the rest of the trail ... More on TrailLink.com

More Reviews

Running parallel to State Route 219, this 4 mile section of trail has been built on a former line of the Pennsylvania Railroad (Line 651) and runs from Sandy Township in Clearfield County (near Tri... More on TrailLink.com

Dia:Beacon

Museums – Beacon, New York

One large set of rooms had blank white canvases. More on TripAdvisor

3.0

9 reviews
2 sources

Average Rating	3.0 out of 5	9 reviews 2 sources
GeckoGo	5.0	1+ reviews
TripAdvisor	3.0

More Reviews

The building itself is nice and open. More on TripAdvisor
I went to the Dia:Beacon last weekend, with very little expectations, and had a fabulous time! I was comple... More on CitySearch

Stockbridge Bowl

Things To Do – Stockbridge, Massachusetts

Fifteen years ago, Stockbridge equated the Red Lion Inn . Today, it's a stop ... More on igougo

More Reviews

'Stockbridge Bowl' is a 372-acre artificially impounded body of water that is 4 km (2.5 mi) north of the village of Stockbridge, Massachusetts. A variant name is Lake Mahkeenac. ... More on Wikipedia
This 372-acre great pond is among the most heavily used in the state. Maximum depth is 48 feet; average depth is approximately 27 feet. Transparency is generally good, running around 13 feet, but i... More on AnglerWeb.com

Mazie's Place

Bars – Throop, Pennsylvania

Harlem Valley Rail Trail

National And State Parks – Millerton, New York

23 miles, 15 open, of scenic, paved walking, rollerblading, biking & cross-country skiing trails; Wassaic - Copake Falls. No horses or motorized vehicles. Access points: Railroad Plaza, Main St./Rt. 44, Millerton, across from gazebo. ... More on iloveny.com

Arlington Farmers Market

Food Shopping – Poughkeepsie, New York

This farmers market displays farm-grown fruits and vegetables, organic cheeses, beautiful flowers, homemade crafts and more. ... More on iloveny.com

Decades Sports Bar

Bars – Swoyersville, Pennsylvania

4.0

1 source

Average Rating	4.0 out of 5	overall rating
CitySearch	4.0	overall rating

Winchester Revolutionary War Memorial

Landmarks – Winsted, Connecticut

Inscription. In Grateful Remembrance, Of the Soldiers of the American Revolution, Who Are Buried, In The Town Of Winchester Stephen Wade Ozias Bronson Wail Loomis John Dare Richard Coit Moses Hatch Roswell Grant Oliver Coe Solomon ... More on HMDB