Main Street Appeal: 5 Walkable Hudson Valley Towns | Sponsored | Community Pages | Hudson Valley | Chronogram Magazine
Listed with Halter Associates Realty, this spacious, light-filled circa 1875 Italianate brick townhome has beautiful period details and is within walking access to everything the Village of Saugerties has to offer
  • Listed with Halter Associates Realty, this spacious, light-filled circa 1875 Italianate brick townhome has beautiful period details and is within walking access to everything the Village of Saugerties has to offer

One of the best parts of living in the Hudson Valley is its quaint and quirky downtowns, which abound with great eats, adorable shops, and historic charm. Lisa Halter, owner of leading Woodstock and Kingston-based real estate brokerage Halter Associates Realty, knows firsthand that the region is chock-full of walkable gems, offering new residents a pitch-perfect blend of city and country life. Here, she recommends five towns with plenty for new homeowners to enjoy on foot.


The eight-block area of Main and Partition streets was the first commercial district listed on the National Register of Historic Places. You’re sure to fall in love with the mix of Victorian, Colonial, and newer ranch homes within walking distance of the village along with its thriving small business scene.

Start your mornings at Ohana Cafe, a breakfast and lunch spot with dreamy crepes and a friendly, down-to-earth vibe. Linger for hours at Inquiring Minds Bookstore & Coffeehouse, where the creaky wood floors complement the intoxicating combo of books and fresh-roasted coffee. And don’t miss a stop at Alleyway Ice Cream, whose inventive flavors (Ovaltine Brownie, anyone?) will have you coming back for more.

Red Hook

Far from the Brooklyn neighborhood that shares its name, this picturesque Dutchess County village just north of Rhinebeck is a hidden jewel tucked among acres of orchards and farms where stately Colonial homes rub elbows with rustic farmhouses.

The intersection of Broadway and Market Street is where you’ll find must-stop shops, including H.A.S. Beane Books, a treasure trove of antiquarian and collectible titles, and Little Pickles Children’s General Store for all your kiddo’s needs. The wood-fired pizza at Lucoli and classic fare at Historic Village Diner are sure to become favorites, too.


Another Dutchess County gem is Millerton, dotted with homes from the 19th century and a downtown reminiscent of an old-fashioned New England town, with shop after shop lining its winding Main Street.

Here, you’ll find the flagship store of tea purveyors Harney & Sons, which has been crafting tasty blends for almost 40 years. At fan-favorite Oblong Books, you’ll always find a new title (or three) to take home and a schedule of author events you won’t want to miss. And for film buffs, The Moviehouse, an independent cinema in a beloved circa-1903 building, will quickly become a household name.


Located just minutes from uber-trendy Hudson, this village on the west side of the river has a treasure trove of shops and restaurants on Main Street and more than enough stately Victorian homes to hold its own.

Find a rotating schedule of art exhibitions along with cafe classics at fun and funky HiLo and stock up on sustainable wares for your home at Kaaterskill Market. It’s just a short jaunt up Bridge Street to Subversive Malting and Brewing, where the hyper-local pours will encourage you to while away the day.


While technically in the Catskills region, the up-and-coming village of Tannersville, long known for its stately ski chalets and picture-perfect cabins in the woods, is definitely worthy of inclusion on this list. The historic downtown shops always had great bones, but when one resident decided to paint her building in an artful assortment of colors, the idea caught on. Now, Tannersville is known as the Painted Village in the Sky.

The one-stoplight Main Street is brimful with offerings ranging from antiques to diverse eats. If you want to shop, but are feeling peckish, you can satisfy both cravings at Last Chance Antiques & Cheese Café. Other must-visits include Rustic Mountain for furniture and handcrafted wares, Bear and Fox Provisions for cafe eats, and Mama’s Boy Burgers & Smiley’s Ice Cream Bar for nostalgia-fueled fare.

To explore these towns with a local agent, contact Halter Associates Realty.

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