Samantha Brown's Favorite Fall Drive

This area in Dutchess County has everything on Sam's fall drive checklist, from wineries and farmers markets to winding country roads and scenic barns.
sam brown leaning against a station wagon during the fall

sam brown leaning against a station wagon during the fall

There are some strict criteria that a fall drive has to meet to be a part of one of the most anticipated times to hit the road. We have our expectations!

My favorite fall drive fulfills every point on my checklist and then some. The agricultural area in Dutchess County in the Hudson Valley of New York has some of the most beautiful land you’ll ever set your eyes on. Winding country roads dip you deep into valleys, where the foliage consumes you, and then lift you above it all, onto the hilltops to reveal a sweeping scene straight out of a painting from the Hudson River School.

Sam's Official Fall Drive Checklist

• Sinuous road, a la a car commercial
• Sweeping vistas
• Elevation changes
• Barns, barns and more barns
• Pleasant farm animals
• Homes you wish you could live in
• Farmers market
• Cool diner for lunch
• Winery

It’s also known as horse country, so you’ll see horses grazing on rolling pastures next to their immaculate barns. And then there are the homes that make you “oooh” and “aaah” as much as the fall colors. You can roll along, enjoying the enchanting farmhouses with fishing ponds, the federalist mansionettes and the turn-of-the-century estates of those who once made a lot of money providing milk to NYC.

To get to this gorgeous region, search “Salt Point, NY” on Google Maps. Then, zoom out and find the main routes, 82 and 44. Use these 2 roads as your bookends, and all the roads in between become your playground. There’s not a bad one in the bunch. Some of my favorite roads to go down are Bangall-Amenia Road, County Road 83 and Carpenter Hill Road. Those 3 will give you a nice taste of all the fall drive criteria. Eventually, you’ll end up back on Route 44, which you can follow to the town of Millerton, NY.

The area has plenty to do and see, of course, but here are 5 of my favorite stops.

Millbrook Vineyards & Winery

Head to Millbrook Vineyards & Winery for a tasting on the beautiful grounds. After you've chosen your favorite wine, knock out your entire holiday shopping list by ordering bottles of it with custom labels. You can even add a family photo, because nothing says “this is why I drink” more than a photo of your kids on a bottle of fantastic wine. 

Village of Millerton, NY

Stretch your legs, walk around and drop some dough in the charming village of Millerton, NY. It’s a quaint hamlet with antique shops and art galleries, including Gilmor Glass, where you can see that the art of glassblowing is alive and well.

Harney & Sons Master Tea Blenders

Harney & Sons' headquarters and factory are just outside Millerton. I know, I thought it was an English brand, too, but it has a beautiful tea shop in town with a tasting room and knowledgeable staff. Choose from 2 full walls of tea, plus the shop sells all types of pots, cups and brew baskets.

McEnroe Organic Farm

McEnroe Organic Farm has a must-visit farmers market. A large sign out front marks what vegetables are fresh from the 1,000-acre family farm. Pour yourself a hot cup of coffee and stock up on the homemade jams and pickles. Party season will soon be upon us, and you’ll need hostess gifts. There are also wonderful fresh-baked goods and old-fashioned doughnuts; those, however, need to be consumed immediately.

Oakhurst Diner

Oakhurst has a perfect diner setting that offers a nontraditional diner menu. Last time I was there, the menu had a nice chicken biryani for dinner. For diner purists, don’t worry; it still serves classic items such as cheeseburgers, vanilla milkshakes and deep-dish apple pie.

MORE: See How Samantha Brown Spends a Regular Day

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