Dutchess County 
Red Hook


The village of Red Hook is located in the northwestern part of the county in the town of Red Hook. The village is only 1.1 square miles and home to 1,961 people.

The village was formerly know as "Lower Red Hook" and the earliest known settlers Nicholas Bonesteel and wife Anna came to the area in 1723. 


Despite the highly recognized Bard College next door in Annandale, the area never strays from its quiet character and charm. Red Hook emanates a uniquely pleasant small-town atmosphere, and when it comes to upstate living, all you could ask for can be found in this sleepy, quaint town. 

Points of Interest 

  • Poets Walk - 776 River Rd, Red Hook, NY - The beautiful walk is two miles of trails through woods and grassy hills. Get inspired or getaway, the walk is truly something special. 

  • Greig Farm - 227 Pitcher Ln, Red Hook, NY - Red Hook is home to one of the Hudson Valley's best farms. You can pick your fruits and veggies, quickly shop at the farmers market, or even sit down for breakfast and lunch (dinner is to-go). Some of the valleys talented performers even host concerts here. 

  • Taste Budd's Café - 40 W Market St, Red Hook, NY- 40 West Market St - The community staple has delicious chocolates and regional musicians. Visit the shop's website for a list of upcoming shows. 



The Village of Rhinebeck was incorporated in 1834. The village exists within the larger Town of Rhinebeck - and covers 1.6 square miles and is home to a population of 2,657. The village is about a two-hour drive from New York City and roughly an hour and a half train ride from Penn Station.


The village has a rich history that dates back to 1686 when the Dutch arrived and bought the land. Years later, in the 1850s, the village grew even further and became known for its woodworking center. Around the end of the 19th century, Rhinebeck became the home of a new industry - the cultivation of flowering violets. The total crop was estimated to be well over a million dollars, and today, the "violet houses" built during the era still stand. 


The main boulevard in Rhinebeck is Montgomery Street lined with local restaurants, bars, and cafes.

Points of Interest 

  • Samuel’s Sweet Shop - 42 E Market St, Rhinebeck, NY - The magic in this little candy shop is special and why it is impossible not to smile when you walk through the door. The place is so unique that back in 2014, it would have closed if it was not for the help of some celebrities, specifically, Paul Rudd. 

  • Terrapin Restaurant - 6426 Montgomery St, Rhinebeck, NY - One of the top restaurants in the Hudson Valley focuses on farm to table dining. 

  • The Old Rhinebeck Aerodrome - 9 Norton Rd, Red Hook, NY - A short drive from the village brings you to the Old Aerodrome. Walkthrough old hangers and look and vintage planes (many of which still fly), and some are over a century old. 



Rhinecliff is a small hamlet 1 mile west of Rhinebeck's town village with a total land area of only 1.1 square miles and a population of just 425. Extensive agriculture and wooded area to the north, east, and south, and the Hudson River on the west surround the hamlet. 

The hamlet was given its name in 1849 by the Hudson River School - the mid - 19th-century American art movement focused on landscape paintings and romanticism. 

Points of Interest

  • The Rhinecliff - 4 Grinnell St, Rhinecliff, NY - Built in 1854 by architect George Veitch - eat, stay, or visit the historic old hotel.

  • Morton Memorial Library -  82 Kelly St, Rhinecliff, NY - The historic brick building along Kelly Street was built in 1905 by Anna L. and Levi P. Morton in memory of their daughter Lena. Dedicated as a library in 1908.

  • Saint Josephs' Mission Church - 18 Loftus Rd, Rhinecliff, NY - Beautiful simple church that sits a top a hill overlooking the Hudson featuring tranquil views.



Incorporated in 1872, Tivoli is 1.5 square miles and has a population of 1,118. The authentic and humble village is part of the town of Red Hook. Diverse architecture, riverfront estates, and many outbuildings make up the area. 

The name came from Peter Delabegarre after obtaining property next to the Livingston estate. Unfortunately, Mr. Delabegarre went bankrupt, but he made plans for a town named Tivoli, and the name certainly stuck. 

The village has excellent cultural and demographic diversity and a substantial market for small businesses. Tivoli's main street, Broadway, hosts several restaurants, shops, and bars. 

Points of Interest 

  • Edgewood Club - 276 Woods Rd, Tivoli, NY - Built-in 1884, this golf club offers terrific views and challenging play.

  • Osaka Japanese Restaurant - 74 Broadway, Tivoli, NY - Enjoy well-crafted sushi rolls, sashimi, and cooked Japanese dishes inside the wood-accented restaurant.

  • Tivoli Art Gallery - 60 Broadway, Tivoli, NY - Painting, photography, sculptures, and more make up the brilliant gallery. About 40 artists operate the gallery and create new exhibits monthly.