The Harlem Valley cuts a north-south swath through eastern Dutchess County. This mainly rural region is characterized by farms and forests, historic settlements and village centers. As you progress northward over three leisurely days, you’ll enjoy a combination of sightseeing, outdoor exploration, shopping, and dining.

S = Seasonal attraction or activity
SE = Open during scheduled events

Day 1: Pawling

Village of Pawling
It won’t take long to explore the shopping and dining district in this charming Victorian village, so you can linger over a cup of coffee or take your time in a cozy bookstore or gift shop. Start on Charles Colman Boulevard, the hub of it all.

Visit Sites of the Historical Society of Quaker Hill and Pawling
Pawling has significant ties to American history, including a presidential candidate, Quaker abolitionist pioneers, renowned journalists, and one of George Washington’s headquarters. You can follow the story by visiting three sites: the John Kane House (Washington’s HQ in 1778); the Oblong Friends Meeting House (the intact 1764 Quaker meeting space); and Akin Hall (three attractions under one copper roof – the Quaker Hill Museum, Natural History Museum, and rare books library). Open seasonally, or by appointment.


Dinner in Pawling
What are you in the mood for? You’ll find casual Irish pub fare at McGrath's Tavern, and classic American cuisine—accompanied by cutting edge cocktails, an award-winning wine list and an old fashioned soda fountain—at McKinney & Doyle Fine Foods Cafe and Bakery.

How about dinner and a show? Rock & Roll Hall of Famer Daryl Hall was inspired by his TV Show “Live from Daryl’s House” to create a venue where people could hang out, have a great meal and listen to amazing musicians in a casual setting, and thus Daryl’s House Restaurant & Live Music Club was born.

Day 2: Dover Plains

Soukup Farms, Dover Plains
Visit this third-generation family owned and operated farm. What began as a hobby has turned into a production that now has over 2,700 taps. Take a tour and experience the maple process as it moves from sugarbush to bottle! And before you depart, be sure to take home some of their delicious specialty maple products from their store including pure maple syrup, maple hot sauce, candies and more. Although the business may be expanding, you’re sure to feel like part of the family at Soukup!

Dover Stone Church, Dover Plains
Take a hike! Convene with the scenic rolling hills and plains of the Harlem Valley before reaching a geological wonder; an ancient cavern framed by large metamorphic rocks. The gothic, pointed arch formation of the stone entrance gave rise to the moniker, “Stone Church.”

Dinner in the area
For a casual bite, try Four Brothers in Dover Plains, where the pizza with a Grecian touch has been the specialty since 1976. For a catered event, try the cozy tavern atmosphere at Old Drover’s Inn, an historic inn which recently went under extensive renovation.  A more formal evening is found in Amenia at Serevan, where Chef Serge Madikians brings together distinctive Mediterranean and Middle Eastern flavors using fresh ingredients from surrounding farms. 

Day 3: Millerton

McEnroe Organic Farm, Millerton
On the drive north on Route 22 to Millerton, you can’t miss this big red farm market. Whatever grows on these 1,000 acres is sold, including a full range of produce and nursery stock. You’ll also find meats, specialty groceries, prepared foods, and fresh baked goods. Or just stop in quick for a cider donut!

Village of Millerton
A hybrid of historic and eclectic, Millerton is a walkable district with shops, cafes, and art galleries galore. At Gilmor Glass, a spacious gallery and studio, you can watch the age-old techniques of creating art glass. Stop into the Harney and Sons tea house to sample a tasting flight of themed teas sourced from across the globe.

The spirit of the independent book seller is alive and well at Oblong Books & Music, established in 1975 and still the largest in the mid-Hudson Valley. Find a signed copy of your favorite novel, attend a book signing, or peruse the music selection. Step back in time at two of the oldest stores in town: Saperstein’s, an old-fashioned clothing and shoe store established in 1946; and Terni’s, which opened in 1919 as a place to shop for hunting gear and fishing tackle. You can still order a milkshake at the marble ice cream counter made in the 1930’s mixer. 

Lunch in Millerton
Time for lunch? Look no further than Main Street, where you can choose from Harney and Sons Tea Shop, Irving Farm Coffee House, the 50’s-era Oakhurst Diner, Taro’s NY Style Pizzeria and more.