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 five 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 classic American cuisine—accompanied by cutting edge cocktails, an award-winning wine list and an old fashioned soda fountain—at McKinney & Doyle Fine Foods 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: Pawling

Pawling Nature Reserve, Pawling 
Take a hike! You’ll be able to access the Appalachian Trail in this 1,060 acre preserve, along with more than ten miles of marked trails that range from moderate one-hour strolls to strenuous day-long treks. In the reserve’s gorge, Duell Hollow Brook cascades down the rocks. At the ridge top, you’re rewarded with stunning views of the Great Swamp and Harlem Valley below.

Day 3: Dover Plains and Wassaic

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
Ready for some more of the great outdoors? 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.”

The Wassaic Project, Wassaic
A collection of unique buildings, including an old mill, provide a home for emerging artists here, specifically in fine art, music, film, and dance. Meet the makers during the Artists in Residence Open Studios days, and come back for the free annual Summer Festival, which features over 100 artists, 25 bands, film screenings, dance performances, and more.

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 cozy tavern atmosphere, try the Old Drover’s Inn, a renovated historic inn dating back to 1750. 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 4: Wassaic and Amenia

World Peace Sanctuary, Wassaic
More than 200,000 Peace Poles that have been dedicated in nearly every country on Earth, through an initiative begun by the World Peace Prayer Society. On the 154-acre grounds of the society’s international headquarters, you’re welcome to visit the Peace Path with 193 peace poles representing each of the U.N. member nations, Peace Labyrinth, globe sculpture, and other points of interest. Grounds open on weekdays.

Wethersfield Estate, Amenia (S)
Visit the former country estate of conservationist Chauncey Devereux Stillman, set at the highest elevation in the area to enjoy far-reaching views. The highlights include the carriage house, trails, the 1939 Georgian-style brick mansion and impressive collection of paintings, and two acres of formal gardens inspired by the Italian Renaissance, complete with resident peacocks, fountains, and a sculpture garden.

Day 5: Millerton

McEnroe Organic Farm, Millerton
You can’t miss the big red farm market on Route 22 between Amenia and Millerton. 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. Have an organic garden at home? You can also purchase their good-asgold compost and top soil!

Village of Millerton
A hybrid of historic and eclectic, Millerton is a walkable district with shops, cafes, and art galleries galore. Stop into the Harney & Sons Tea Shop 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.  

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