Directions from Cambridge, Massachusetts to New Paltz, 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.


21 West

Bars – Dudley, Massachusetts

21 West - If you’re planning on wearing sneakers, hoodies or any other casual apparel, you should probably go to another lounge. 21 West, located at 21 W Main St prides itself on ... More on clubzone

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Holiday Mountain Ski & Fun Park

Themeparks – Thompson, New York

Fun park featuring go-karts, bumper boats, bumper cars, rock wall, mini-golf, potato sack slide, arcade, Choo Choo Charlie, mechanical bull ... More on iloveny.com

Juniper Hill Golf Course

Golf Courses – Northborough, Massachusetts

I've played both but prefer the Lakeside because it's much more challenging with treed fairways...tee shots over water or swamp etc..the Riverside is very open and reminiscent of olde New England..... More on GolfReview

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  • Well kept and not very penal. More on golflink.com

  • Juniper Hills Riverside A pleasant course to play. Well kept and not very penal. Some interesting shots. Great hot dogs!! More on golflink.com

Dublin Ale House

Bars – Naugatuck, Connecticut

Dublin Ale House, located at 1221 New Haven Rd # 4, is your garden variety pub. It’s not going to win any raves of "Hottest. Bar. Ever.," but it’s a serviceable place to relax and unwind. Just keep your expectations ... More on clubzone

3.5
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Taconic State Park, Rudd Pond Area

National And State Parks – Millerton, New York

Taconic State Park is a well-kept, inexpensive, conveniently-located campground in upstate NY. More on Epinions.com

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  • Taconic State Park is a well-kept, inexpensive, conveniently-located campground in upstate NY. The campgrou... More on Epinions.com

  • 225 acres, 40 campsites w/hot showers. RVs up to 20-foot accepted. Beach w/swimming, boat rentals, childre... More on Dutchesstourism.com

Guard House

Landmarks – Redding, Connecticut

Inscription. On this site stood the Guard House of 1778-9. A soldier was shot & killed by the sentry on duty when attempting to escape. , Location. 41° 20.222′ N, 73° 22.742′ W. Marker is in Redding, Connecticut, ... More on HMDB

Round Ball Mountain Conservation Area

National And State Parks – Ancram, New York

105.6-acre property offering spectacular views of the Harlem Valley and the Taconic Mountains. The summit is 1,318 feet, with a gentle ascent on one side with other areas characterized by steep slopes, rocky ... More on iloveny.com

Woodland Wildling Garden

Gardens – Harris, New York

A 3 acre botanical garden containing over 500 plants, shrubs and trees. More on iloveny.com

Pratt Pond

Themeparks – Upton, Massachusetts

Pratt Pond is a small eutrophic, warm water pond located in Upton and draining into the Blackstone River. Depth averages six feet with a maximum of 16 feet. The bottom is about three-fourths muck with the remainder evenly divided ... More on AnglerWeb.com

Bridge: Twin Hills Country Club

Golf Courses – Bolton, Connecticut

(Twin Hills Country Club, 30', 1985, 07-07-c) across Ash Brook at the 5 th hole in Twin Hills Country Club NW of Coventry , Coventry Township, Tolland County, CT. CT31 NW 4.2 miles from jct with CT275 in Coventry, W. on US44/CT31 ... More on dalejtravis.com

A Latte More

Restaurants – Middlebury, Connecticut

I would highly recommend going here for lunch or a snack....and an espresso. More on Yahoo! Travel

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  • BEST COFFEE I'VE HAD IN A LONG TIME GREAT ATMOSPHERE DELICIOUS STRAWBERY TART More on Yahoo! Travel

  • Best coffee I've had in a long time great atmosphere delicious strawbery tart More on Yahoo! Travel

Emilia's Restaurant

Restaurants – Danbury, Connecticut

Ward Pound Ridge Reservation

Things To Do – Cross River, New York

The Pound ridge reservation offers a few surprisingly fun possibilities, both for bouldering and trad. An area known as Leatherman's cave has a few steep walls with accessible walk arounds for top ... More on RockClimbing

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  • 4,700 acres, wooded, hilly. Nature preserve, 35 mi of hiking trails, river flows through park. 23 leantos, 10 tent sites. ... More on iloveny.com

Dunkin' Donuts

Donuts – West Hartford, Connecticut