Dutchess County 
Millbrook

History

Located on the east side of the Hudson River about 90 miles north of New York City is Millbrook - a village in Dutchess County. The village has a total area of 1.9 square miles and a population of 1,452 people. Millbrook is often compared to that of a low-key version of the Hamptons.

The village was once home to Bennett College (closed in 1978), and Timothy Leary, who lived on the Hitchcock Estate and wrote "The Psychedelic Experience" during the 60's. 

The village comes to life on the weekends as locals and visitors relax at restaurants and stores along Franklin Avenue. Millbrook has a strong sense of community, and continues to be one of the most popular places to live and stay in the Hudson Valley.

Points of Interest 

  • Franklin Avenue - The main street of the village is home to multiple antique shops, the most famous being the Millbrook Antiques Mall - the store is three stories and features antiques at all price points. And of course the street is lined with great dining and other shopping options for all to enjoy. 

  • Tribute Gardens - 21 St. Joseph’s Dr - Take a beautiful stroll through the garden that features two war memorials and a quiet green in the back that is great for picnics. The beautiful landscaping is regularly maintained and the top area of the park features a special view of the village below.

  • Bandshell - 3327 Franklin Ave - The Millbrook Arts Group puts on Saturday night concerts on the green behind the historic Thorne Building. 

Millerton

History

Millerton is a small village in Dutchess county home to 958 people and only 0.6 square miles in size. Millerton was named one of "The Ten Coolest Small Towns in America" by Travel Magazine in 2007. 

The town has a prime location surrounded by rustic farms and state parkland. The towns past is still felt in the quaint but vibrant downtown -the Moviehouse is located in a 110-year-old building that features a striking clocktower from years ago. Furthermore, several clothing boutiques, florists, jewelers, and of course antique shops are all packed into the villages Main Street. 

Millerton is unique and full of character making it a great place to live and even better place to escape the hustle of the city.

Points of Interest 

  • 52 Main - 52 Main St, Millerton, NY 12546 - One of the areas best new restaurants - 52 Main is a tapas bar/eatery that offers global wines in a casual lounge with live music.

  • Harney & Sons Fine Teas - 5723 NY-22, Millerton, NY - One of the more popular destinations for visitors has always been Harney & Sons for its unique tea tasting room and inviting lunch menu.

  • Harlem Valley Rail Trail -  Starting at the Wassaic Metro-North station is 10.7 miles of paved pathway perfect for walking, running, and biking.

Red Hook

History

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. 

Rhinebeck

History

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

History

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.

Tivoli

History

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.