Directions from Dennis Port, Massachusetts to Rhinebeck, New York





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.


Air Park Drive-In

Parks – Highland, New York

Screens: 1 Sound: Car Capacity: 292 Typical season: Technical details: none Air Park Drive-In Timeline: There are no timeline ... More on drive-ins.com

Beacon Reservoir (Dutchess County, New York)

Lakes – Beacon, New York

'Beacon Reservoir' supplies water to the city of the same name in Dutchess County, New York, USA. It is located at 1,285 feet (392 m) above sea level in a hollow between Beacon Mountain and Scofield Ridge, in the neighboring Town ... More on Wikipedia

Pastime Athletic Club

Bars – Chicopee, Massachusetts

Pastime Athletic Club - Of the city’s hundreds and hundreds of bars, Pastime Athletic Club fits right in the middle of the bell curve – a place to hit with your buddies on the way to your ultimate destination. ... More on clubzone

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The Jaguar Path

Health Club – Great Barrington, Massachusetts

The Jaguar Path is a training in the use of the yogic science and philosophy as energy medicine. Sourcing from yogic and shamanic traditions, this work enables individuals and healers to understand and activate their innate healing ... More on YogaFinder

Mount Washington House Tavern

Bars – Hillsdale, New York

Mount Washington House Tavern - Sometimes you just don’t want to pay $12 for a drink. On those nights, head out to Mount Washington House Tavern, located ... More on clubzone

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All Seasons Vending

Things To Do – Agawam, Massachusetts

Methodist Church

Landmarks – Pawling, New York

Inscription. First church built in 1809, South Road; second church, in 1854 on Main Street. This church erected in 1864. Additions in 1928 and 1960. , Erected by Pawling United Methodist Church. , Location. 41° 33.689′ ... More on HMDB

Catamount Ski Area

Ski Resorts – South Egremont, Massachusetts

All in all Catamount is a great bargain (given a day trip can be made easily without the need for an exp... More on SkiTown.com

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  • All the trails generally come back to the base so it is easy to meet up with friends of a run or two and th... More on SkiTown.com

  • SkiTown Review Ski resort reviews can be helpful only if you know the skill level and skiing perspective of... More on SkiTown.com

Mount Washington State Forest

Nature Scenery – Copake Falls, New York

'Mount Washington State Forest' is a scenic state forest in the southern Taconic Mountains of the southwestern Berkshire region of Massachusetts. It has 30 miles of trails for hiking, as well as offering wilderness camping, fishing, ... More on Wikipedia

Greig Farm

Things To Do – Red Hook, New York

great place for picking apples (good selection), berries (raspberries and blackberries) in summer and also ... More on TripAdvisor

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  • Apple and pumpkin picking at the Greig Farm in Red Hook, NY, is fun, accessible and the produce is excellen... More on TripAdvisor

  • Pick your own peas, blueberries, blackberries, fall raspberries, pumpkins. See website for schedule. More on iloveny.com

Gold Mine Saloon

Restaurants – Wawarsing, New York

Domino's Pizza

Restaurants – Saugerties, New York

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Panera Fresh Dough Facility

Restaurants – Franklin, Massachusetts

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Ashumet Pond

National And State Parks – Mashpee, Massachusetts

Ashumet Pond is a 203-acre natural kettlehole pond with an average depth of 23 feet and a maximum depth of 65 feet. The ponds water sources are groundwater and an inlet from an abandoned cranberry bog. Transparency is good, averaging ... More on AnglerWeb.com