Directions from Wildwood, New Jersey to Pittsfield, 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.

Lilac Park

Parks – Lenox, Massachusetts

Town picnic and rest area - Recently restored by the Lenox Garden Club to its original collection of ... More on Lenox.org

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Town picnic and rest area - Recently restored by the Lenox Garden Club to its original collection ... More on uptake_content

Bashista Orchards

Farm – Southampton, Massachusetts

Visit our country store for: Fresh fruit and vegetables, Store baked pies and breads. Those awesome Cider Donuts! Local maple syrup and honey. Preserves, crafts and gifts. Mapleline milk and dairy products, free range chicken eggs, ... More on allaboutapples.com

Mt. Sugarloaf State Reservation

Parks – South Deerfield, Massachusetts

300 Sugarloaf St. S. Deerfield MA 01373 413 665-2928 Mt. Sugarloaf offers a commanding view of the Connecticut River, the Pioneer Valley, and the Pelham and Berkshire Hills. Consisting of two peaks... More on Mass.gov

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Mt. Sugarloaf offers a commanding view of the Connecticut River, the Pioneer Valley, and the Pelham and Berkshire Hills. Consisting of two peaks, North and South Sugarloaf, the Reservation offers p... More on Epinions.com

Ship Ahoy Beach Club

Things To Do – Sea Bright, New Jersey

Queechy Lake

Lakes – Richmond, Massachusetts

'Queechy Lake' is a lake in Canaan, Columbia County, New York. Situated near the Massachusetts state border, the lake is deep and contains a surface area of 141 acres. The lake is located near two major roads, New York State Route ... More on Wikipedia

The Colony

Landmarks – Monroe, New York

Inscription. Founded in 1919 by Sterling Forest Farms Corporation as the first African-American vacation community in New York State. , Erected by Greenwood Forest Farms Association. , Location. 41° 14.592′ N, 74° ... More on HMDB

Soul Power Yoga

Health Club – Marlboro, New Jersey

Revolutionary yoga classes for adults, kids and teens! More on YogaFinder

Johanna's Motel

Things To Do – Copake, New York

Large comfortable rooms and a scenic location await guests at this conveniently located motel. More on iloveny.com

Prospect Lake

Beaches – North Egremont, Massachusetts

The Town of the Ancient Trees" When the first English settlers came to Sheffield in 1725-26 they found a number of Dutch settlers with substantial farms in what is today Egremont. Dutch claims to the area arose under the 1722 Patents ... More on GoingToTheBeach.com

Manny Welder Park

Things To Do – Monsey, New York

Several tennis and handball courts, ball fields, children's playground, nature area, biking and jogging paths. 8 Tennis Courts 4 Handball Courts 4 ... More on KidsPlayParks