Directions from Rockport, Massachusetts to Poughkeepsie, 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.


Mill House Antiques

Things To Do – Woodbury, Connecticut

Originally an 18th Century grist mill, Mill House Antiques can be found nestled in a gentle bend of the Nonnewaug River along Route 6 in northern Woodbury, Connecticut. Established in 1964 as a des... More on Millhouseantiques-ct.com

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  • Mill House Antiques and Gardens - More than an oridinary experience More on Millhouseantiques-ct.com

Wellesley Historical Society

Museums – Wellesley Hills, Massachusetts

Commander

Things To Do – Cornwall on Hudson, New York

Narrated excursion cruises aboard m/v Commander (on National Historic Register). Snack bar. Departing West Point Mon-Fri 12:30PM, and first Sunday of the month. Departing Haverstraw Marina 10AM. R... More on Orangetourism.org

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  • Narrated excursion cruises aboard m/v Commander (on National Historic Register). Snack bar. Departing West Point Mon-Fri 12:30PM, and first Sunday of the month. Departing Haverstraw Marina 10AM. Re... More on Orangetourism.org

Delaware & Hudson Canal Museum

Museums – High Falls, New York

The museum displays nearly 4,000 objects from the Delaware & Hudson Canal's construction, and maintains a walking trail to five of the original canal's locks. Nearly 4,000 artifacts maps, models, paintings, and documents relating ... More on Heritage

Breezeland Orchards

Farm – Warren, Massachusetts

Cider mill. Containers provided. Bring the whole family. Cider, donuts, corn, pumpkins. Buses welcome. More on allaboutapples.com

Old Bethel Road

Things To Do – Bethel, Connecticut

It was a relaxing ride, first time out this year so it was good for beginning of the year legs. More on trails.mtbr.com

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  • If you like rocky double-track riding this one's for you. This is a beautiful ride in the back country. The trail has some sections that are fast, some that are sandy, some that are rocky, and a fe... More on trails.mtbr.com

  • It was hard to find with a gps, ended up in someones strawberry fields at first ; ) eventually we found it. It was a relaxing ride, first time out this year so ... More on trails.mtbr.com

Center Springs Park

Parks – Manchester, Connecticut

This camouflaged PlayBooster® cant hide its challenging, enjoyable events. The Curved Track Ride, Loop Horizontal Ladder and Disc Challenge are three events that once are revealed, ... More on KaBoom.org

zipcar

Things To Do – Brighton, Massachusetts

about zipcar: Boston residents understand the expense involved with owning a car in the city. Zipcar is the perfect solution for non-car owners who'd like to hop in a car for a trip to the market or the beach for a day. This service ... More on GoCityKids

Newtown Meeting House

Landmarks – Newtown, Connecticut

Inscription. Newtown Meeting House, Has Been Placed On The, National Register, Of Historic Places, By The United States, Department Of The Interior, Built 1720Moved 1792Rebuilt 1816 & 1845, , Loca... More on HMDB

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  • Art Gallery Check out waterclors by a local artist, Ruth Newquist. These are available for purchase. Learn more... Support Us! The Newtown Meeting House is administered and financed solely by Herit... More on Newtownmeetinghouse.com

Dover Historical Society

Museums – Dover, Massachusetts

The Town of Dover began as the Fourth Precinct of Dedham, Springfield Parish, in 1748. It was separated as the District of Dover in 1784 and became the Town of Dover in 1836. The history of Dover can still be seen in buildings and ... More on MuseumsUSA.org

Cronomer Hill Park

Tennis – Newburgh, New York

This park features both passive and active recreation areas. The lower portion of Cronomer Hill Park features several multi-purpose ball fields and t ennis courts, while the upper portion of the park features an observation tower ... More on KidsPlayParks

The Funky Monkey Cafe & Gallery

Restaurants – Cheshire, Connecticut

I enjoyed the cheese platter that was served very much and the music combo was great too but the interior was beautiful. I loved the colors so crisp and new. I would highly reccommend it as ... More on Yahoo! Travel

Troutbeck

Restaurants – Amenia, New York

A regular "a la carte" lunch, dinner Wed-Sat, Sun brunch. Weekend reservations required. Closed Mon & Tues. More on iloveny.com

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  • Troutbeck is a beautiful and lush forty-three acre resort in the picturesque foothills of the Berkshire Mountains. The grounds include towering 200 ... More on Troutbeck.com

Mazury Polish Deli

Restaurants – Meriden, Connecticut

Sarah Whitman Hooker House

Museums – West Hartford, Connecticut

In the southern end of town, visit the historic Sarah Whitman Hooker House, a carefully restored early ... More on Westhartford.org

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  • West Hartford also has a couple of those restored houses that are ubiquitous in Connecticut. The Sarah Whitman Hooker Homestead is a lovely 1720 mansion named for a resident heroine of the ... More on Off the Beaten Path: Connecticut