Page 32 - 2025 Westchester Relocation & Moving Guide

DUTCHESS COUNTY
You may have visited Dutchess for its popular county fair, but this area has so much more to offer. Whether you’re exploring historic sites like Franklin D. Roosevelt’s home in Hyde Park or getting in tune with nature at Millbrook's Trevor Zoo, there is never a shortage of things to do.
􏰁 BEACON
Countless towns across the Hudson Valley are havens for all sorts of creatives, and Beacon is no exception—in fact, this river city has seen a boom in popularity over the past two decades. Its past as an industrial hub is still evident on Main Street, where 19th century buildings are now chic condos and clothing boutiques, art studios, and eateries. Among the many shops you’ll want to check out are the floral and décor store Raven Rose, Hyperbole, Vintage: Beacon, Zakka Joy, and Witch Hazel.
The restaurant scene is flourishing as well. Grab a bite at The Roundhouse, a boutique hotel with a farm-to-table restaurant, Kitchen & Coffee, a gluten-free and vegetarian café that also serves craft espresso drinks, Beacon Falls Café, an American bistro with a great brunch menu, or Beacon Bread Company.
Outdoor destinations like Long Dock Park and Mount Beacon are only minutes away from Main Street. A beloved farmers market with local purveyors occurs year-round on Sundays at 223 Main Street. And no trip to Beacon would be complete without a visit to Dia Beacon— one of the largest contemporary art museums in the country.
􏰀 WAPPINGERS FALLS Love Beacon but can’t justify the prices? Wappingers is a popular choice for a similar vibe. It’s on the Metro-North line, has a great selection of places to dine, and plenty of recreation.
Plus, it’s a short drive to Beacon, Cold Spring, and Poughkeepsie and near both I-84 and the Taconic State Parkway. Many NYC transplants are relocating here— especially those who like green space and walkability.
􏰀 POUGHKEEPSIE This city is one of the many beating hearts of the Valley. It’s got the best of both worlds for commuters and families who want a central location and fair prices. Overall, Poughkeepsie attracts a diverse group of buyers who are seeking walkable downtown areas, suburban acreage, and cultural amenities. Poughkeepsie is also
the home of Vassar College and its excellent Frances Lehman Loeb
Art Center, Walkway
Over the Hudson State Historic Park, the 200- acre, circa 1851 Locust Grove Estate (which was the home of Samuel F.
B. Morse, inventor of the telegraph, and boasts
a museum, trails, and a nature preserve), and the great-for-kids Mid-Hudson Discovery Museum.
􏰁 MILLERTON
A refreshing balance of
bustling village and rural charm, this Dutchess County town is a gem.
If you’re an outdoor enthusiast, you will love Millerton—the entrance to the 26-mile Harlem Valley Rail Trail is right on Main Street, perfect for walking and cycling. Five minutes north of the village is Rudd Pond in Taconic State Park, a popular spot for fishing, swimming, and kayaking.
Main Street is home
to the headquarters of
two national beverage brands: Harney & Sons
tea and Irving Farm coffee. Restaurants include the retro Oakhurst Diner,
The Millerton Inn, and Willa. The village also
has a diverse shopping scene: Oblong Books and Oblong Jr., Westerlind for outdoorsy clothing, and furniture stores including Hunter Bee, Montage Antiques, and the Millerton Antiques Center.
􏰁 RHINEBECK From the time Dutch
settlers came to the area in the 1600s, Rhinebeck has been constantly evolving. Today, it's a cultural hub
of northern Dutchess that has something for everyone.
A shopping hotspot, Rhinebeck’s stores include Hammertown for furnishings; Oblong Books; StarryBird Kids; and Samuel’s Sweet Shop, owned by resident celebrities Jeffrey Dean Morgan, Hilarie Burton, and Paul Rudd.
Along the tree-lined streets, you’ll also find excellent eateries: Terrapin for farm-to-table; Cinnamon for Indian fare; Aba’s Falafel; Le Petit Bistro; and many more.
Rhinebeck is near Ferncliff Forest, Drayton Grant Park, and the
Vlei Marsh Preserve
for outdoor fun; and
the Dutchess County Fairgrounds hosts events throughout the year.
􏰁 TIVOLI
Quiet, quaint, and hugging the banks of the Hudson with views of the distant Catskill mountains, Tivoli is the epitome of charm.
What makes Tivoli so popular is its combination of young professionals, students from nearby Bard College, and high-profile locals like actor Mary Stuart Masterson. The owners of Fortunes Ice Cream, Thrift 2 Fight, and the original directors of Kaatsbaan Cultural Park, are all Bard alumni.
The village boasts a vibrant arts community, made up of Kaatsbaan, the Hessel Museum of
Art at Bard College, and Tangent Theatre Company. There's also Tivoli Bays
for hiking, swimming, and boating, and excellent restaurants including Giobatta Alimentari;
Rojo Tapas + Wine; and Traghaven Whiskey Pub, which boasts the largest selection of Irish whiskey in the country.
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