A road trip guide to Dutchess County, one of Upstate New York’s best kept secrets.
Rolling pastures, cool shops, and an interconnected community of classic American towns.
Here’s where you’re going:
Poughkeepsie > Clinton Corners > Bangall > Stanfordville > Pine Plains > Millerton > Rhinebeck
It may seem like a lot, but everything is close together. You’re basically doing one big loop through Dutchess County and taking in some of the best spots along the way. See the Google Map at the bottom of this post, where I plotted out the course. And remember, most of the businesses in Upstate NY are open from from 9am-5pm. 6, if you’re lucky. So grab your coffee and let’s hit this.
Drive to Poughkeepsie and get brunch at Brasserie 292. Incredible food, beautiful interior, and a friendly/stylish staff (Look for the bread table in the back. It’s heaven on a butcher block.) Afterward, walk it off on the Walkway Over the Hudson – the longest pedestrian walkway on earth, spanning one of the widest parts of the Hudson River.
The walkway is free, with donation boxes along the way. Bring a camera. And a windbreaker.
Salt Point & Clinton Corners:
Hop in the car and drive up 9G towards Hyde Park. Take a right at the Rite Aid onto Crum Elbow Road. Wind your way to the end, and keep an eye out for the alpaca farm on the right just before you hit Salt Point Turnpike (Rt. 115).
Take a left on Salt Point Turnpike, and take it all the way through Salt Point, past the onramp for the Taconic State Parkway. Just past the onramp you’ll see a Stewarts Gas Station on the right and Agway on the left. Right after the Agway, there’s this little sign for ANTIQUES. It’s basically a dilapidated barn with a random assortment of things the farmer and his son have collected around the area.
Bangall & Stanfordville:
Get back in the car and keep driving down 115 until it ends at Route 82. Take a left and head north on 82. Keep an eye out for a little sign for Bangall on your right. Veer right towards Bangall. It’s a tiny hamlet.
Turn into the parking lot of Red Devon and head next door to NL/GB, a beautifully curated store dedicated to the modern country home. The co-owners are from The Netherlands (NL) and Great Britain (GB), and it comes through in the elegant mix-and-match aesthetic.
Get back in the car and take a left out of the parking lot, heading back the way you came into Bangall. Take a right on 82 heading north. Keep an eye out for a hideous neon green antique shop called Ole Carousel Antiques Center on your right. Don’t let the color fool you. This place is a gem. And the prices are right.
Pine Plains (Part 1):
LUNCH – You have a few options, but there are two that I’d highly recommend. Get back in the car and head north on 82 into Pine Plains. If you’re in the mood for an amazing meatball or chicken parm sub, hit Sonny’s, a little roadside tavern just a little ways up from Ole Carousel, on the right. They’re known for their incredible red sauce. Or, another favorite lunch spot is The Stissing House in Pine Plains. Excellent, casual french-influenced tavern fare. They’re lamb burger is outstanding, and the interior is beautiful: a dining room dating back to the Revolutionary War, but with an open plan that doesn’t feel stuffy.
At four corners in Pine Plains (where The Stissing House is situated), turn right onto Route 199. Stop at Peck’s Market if you need any provisions. Great little family-run farm market stocked with everything you could ever want.
Keep driving out of town, keeping an eye out for the LEAVING PINE PLAINS, COME AGAIN sign on the side of the road. Just past the sign on the left, look for HAMMERTOWN – it’s kind of hidden.
This is one of my favorite shops in Upstate NY. They have one in Rhinebeck and Gt. Barrington, MA. Their motto “Love where you live” sums them up perfectly. Incredible sense of style. Anything you buy will make your home or apartment feel like you’re getting it ready for a catalog shoot. Organic soaps, anyone?
Get back on 199 and keep driving east to where it ends at Rt. 44. Look left. Harney & Sons Tea. Yes, that’s where they make it. But you can’t buy any here, you’ll need to keep heading into Millerton for that. Take a left onto Route 44 and take it into Millerton. Turn right onto Main Street and find a place to park.
Pine Plains (Part 2):
Get back in the car and head back the way you came taking Route 44 back to Route 199, taking a right on Route 199 heading back to Pine Plains (we’re now heading West to see that whole side of Dutchess). Pass through Pine Plains 4 corners and keep an eye on your right for Pine Plains Fine Wines & Spirits. My favorite wine shop. Have the owner, Will, help you pick out some things. And make sure you pick up at least one bottle of his own wine with his dog on the logo.
Leaving the wine shop, turn right onto 199 and follow it west, past the Taconic Parkway, veering left at the fork onto Route 308. Take 308 all the way into Rhinebeck. This is where you want to be to round out the day. For coffee, you want Samuel’s (who also do killer molasses cookies). For antiques, hit the Antiques Market in the big red barn behind the Beekman Arms. For cool hipstery hand-crafted furniture, hit Sawkille. For interesting menswear, Changes. And if you didn’t get to check out Hammertown or Oblong Books earlier in the day, they have a couple outposts located right next to each other.
For dinner in Rhinebeck, you want Terrapin (culinary American in a remodeled church), Gigi’s (culinary Italian), Le Petit Bistro (excellent French), Arielle (incredible, diverse French/European/Colonial menu with a beautiful interior and solarium), or Aroi Thai (better than any of the Thai places I frequent in NYC).
Catch a movie in Hyde Park at the old school Roosevelt Cinemas (can’t beat the prices), or hit the Hyde Park Drive-In (not only is it fully functioning, but it’s incredibly popular, and not in an annoying way). Afterwards, grab a midnight snack at The Eveready Diner.
All photos by Sparrow Hall
View Favorite Routes: Dutchess County Antiques & Eats in a larger map