If you’re looking for things to do in Dutchess County, especially on a beautiful summer day, you’ll find plenty of places to spend time outdoors. Located in the Hudson Valley about 90 miles north of New York City, Dutchess County is a place of steep valleys and panoramic views, dotted with horse and dairy farms. It’s made up of a handful of towns and hamlets, with the Appalachian Trail running through a couple of them.
Dutchess County is east of the Hudson River and just a few miles west of the Connecticut border.
A couple of summers ago, some local friends took us on a one-day tour to some of their favorite places. It was one of those days in June with a deep blue sky and an early summer breeze, and it was so memorable that Matt and I recreated it in early September, eager to capture the sense of space and freedom and beauty that seemed so precious after March of 2020.
Our second trip—though our friends were unable to join us this time—did not disappoint. There are endless gorgeous Dutchess County destinations, so narrowing it down isn’t easy, but here are recommendations for passing one perfect day.
1. Dover Stone Church
Our first stop was a short hike to Dover Stone Church, whose name becomes obvious once you reach it. Giant slabs of rock have naturally come together at the mouth of a small cave to form a cathedral-like entrance. Inside the dark cave, shafts of light shoot down from cracks in the rock formation above, and a 30-foot waterfall rains down at the back.
This hike is short and sweet, and while the waterfall inside Dover Stone Church isn’t huge, the payoff of reaching this natural wonder is.
How to Get to Dover Stone Church
Driving along Route 22, it’s easy to miss the path that leads to Dover Stone Church. Keep an eye out for a café called Freshco 22 (3156 NY Route 22), located inside a small shopping plaza called Ketcham’s Corner.
This is one of the designated parking lots for visitors (see below for additional parking). Cross the street and go to the blue historical marker identifying the spot as Dover Stone Church and walk up the gravel driveway. From the top of the driveway, take the steps leading to a long straight path lined with trees and surrounded by a meadow of wildflowers.
Follow the path for just under half a mile until you reach the trailhead kiosk. Here you can read up on the history and formation of Dover Stone Church and see a map of the area’s trails. From here, follow Stone Church Cave Trail to see the main attraction, or follow one of the other three trails indicated on the kiosk.
The walk to Dover Stone Church is not difficult, but there are a lot of uneven, potentially slippery rocks along the way, so sturdy sneakers or hiking boots are in order.
- Address: 3128 NY-22, Dover Plains, NY
- Additional designated parking lots: Dover Elementary School (when school isn’t in session): 9 School Street. Tabor-Wing House: 3128 NY Route 22
- Admission: FREE
2. Innisfree Garden
Visiting this exquisitely landscaped public garden has to be one of the most serene things to do in Dutchess County.
Near the parking lot, there’s a small welcome center where a kind employee told us there were two experiences not to be missed at Innisfree Garden: exploring the Japanese garden and following the path around the lake.
This was good advice, especially considering the 185-acre size of the property—having a couple of destinations in mind was useful. It’s also how the landscape is meant to be explored. Innisfree Garden was designed after a concept called “cup gardens,” a style derived from an 8th century poet, painter, and maker of gardens named Wang Wei.
Where Western gardens are laid out in their entirety, this style includes many “garden vignettes” that provide episodic experiences for the viewer, which are all, ultimately, connected to the whole.
To my amateur eyes, this layout meant there were lots of different, cool things to see. We spent a lot of time in the Japanese garden and then finally pulled ourselves away to walk around the lake, which was covered with lotus flowers in bloom. There are plenty of benches and chairs scattered about when you’re ready for a rest, and we passed more than one artist attempting to capture the sheer beauty that surrounded us.
- Address: 362 Tyrrel Rd., Millbrook, NY
- Admission: Adults: $10. Seniors (65+) and Children (5-15): $5. Members and Children 4 and under: FREE
- Check business hours
3. Millbrook Vineyards & Winery
On what used to be Wing Dairy Farm, 30 acres of grape vines grow at a beautifully scenic winery in the Hudson Valley. It’s so serenely peaceful at Millbrook Vineyards that I would return again and again if I lived nearby.
The winery is open year-round so your experience will depend on the weather.
On a warm summer weekend, there might be a local food truck on the premises, and a live band playing. Feel free to bring your own picnic, along with a blanket or lawn chair to make yourself comfortable, or just snag one of the many picnic tables scattered around. Bottles of wine are available for purchase—they’ll provide you with plastic cups if you want to consume it on the premises.
Wine tastings are available any time of year but one is definitely in order during colder weather. This happens inside the restored Dutch barn that serves as the winery’s main building. Beer and wine, as well as non-alcoholic beverages and light snacks are available for purchase on the first floor.
On the second floor is a wide open space with a bar with drinks served by the glass, and plenty of comfortable places to sit, including a deck with sprawling views of the property.
You can also grab a map inside the main building and then follow the walking trails along the property. The house you see on top of the hill, above the ponds, is Wing’s Castle, a quirky bed and breakfast that’s featured on the Haunted History Trail of New York.
- Address: 26 Wing Rd., Millbrook
- Hours: Open daily year-round 12 p.m.-5 p.m.
- Read about guided wine tastings
4. The Lantern Inn
We worked up an appetite from our epic day in beautiful Dutchess County, so our friends took us to eat in the outdoor garden at the Lantern Inn in Wassaic. They serve a pretty amazing burger and have a great selection of beers.
- Address: 10 Main St., Wassaic
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