Community Meets Luxury

The Perfect Dutchess County Day Trip

July 20, 2022

Whether you’re exploring the LaGrange area as a possible new place to live, or simply craving a change-of-scenery adventure, southeastern Dutchess County makes for the perfect day trip destination.

Thanks to easy access from the Taconic Parkway and I-84, this neck of the woods is only 1 ½ – 2 hours from Manhattan, Brooklyn, Westchester, and even northern New Jersey. Here we’ve mapped out our ideal Dutchess County day trip itinerary…

Take a Scenic Drive: The Taconic Parkway
If all you know of “The Taconic” is its narrow, commuter-crowded southernmost section, then you’re missing out on a truly classic American road. Here in Dutchess, the Taconic widens out, slows down, and fulfills the destiny Franklin D. Roosevelt envisioned for it: a scenic park-like roadway that moves and grooves with the shape of the land. Gorgeous vistas, courtesy of the county’s farms, woods, hills and valleys, await drivers around each bend and over each rise. For daytrippers and locals alike, the historic Taconic is “the mother road.”

Have a Heroic Breakfast: The Daily Planet
Too often, the road tripper’s desire to pack the day full of activities means that breakfast ends up being gas station coffee and a pre-wrapped muffin. Instead, make the morning meal into one of the highlights of your visit by spending an hour at the popular Daily Planet in LaGrangeville. As the comic book name hints, this classic-style diner melds traditional stainless steel with “The Man of Steel” for a fun pop décor, including a custom painted Metropolis-style phone booth. But what’s really super here is the friendly waitstaff and the all-American diner fare.
1202 Rte 55, Lagrangeville; www.dailyplanetdiner.com

Shop and Stroll in Millbrook
If you feel like getting out of the car and putting your feet on the concrete, the lovely village of Millbrook is just the place to take a midday stroll and do some shopping. Among the many go-to destinations for oddball knick-knacks and sure-to-please gifts are The Millbrook Antique Center and Millbrook Antique Mall; both locations house several dozen individual sellers of vintage ephemera for all tastes and budgets. Even if you don’t find anything to buy, Millbrook is a treasure in itself, and the beautifully landscaped Tribute Gardens park is the perfect place to just sit, relax, and enjoy the panoramic view of a picture-perfect American village.

A Big Lunch at Big W’s
Great food in generous portions are what they do best at Big W’s Roadside BBQ in Wingdale, where ribs, pulled pork, beef brisket, and barbecued chicken are served up with all the expected side dishes. The Harleys you’ll see in the parking lot attest to the quality of the food, and the always warm staff will go out of their way to make you feel welcome. Regulars recommend the baked beans, and newcomers are reminded that leftovers will likely be enough for an entire second meal.
1475 Route 22, Wingdale; www.theforkingpig.com

Take a Hike: Pawling Nature Reserve
Work off some of those lunchtime calories with a walk in the gorgeous Pawling Nature Reserve, 1000 acres of pristine forests, fields, meadows and marshes located in the towns of Dover and Pawling. Streams, pools, and waterfalls provide backdrops for your perfect photos, and quiet walkers may get a chance to snap pics of deer, coyotes, and even bobcats. The national treasure of The Appalachian Trail crosses through the reserve, so you may even spot the elusive creature known as “the serious hiker.”
Quaker Lake Road, Pawling; www.pawlingnaturereserve.org

Something Sweet: Zoe’s Ice Cream Barn
Talk about Dutchess County flavor, both figuratively and literally: Zoe’s is a charming local favorite, offering up fresh ice cream made daily using only fresh Hudson Valley ingredients – which you can watch being made through an observation window — along with other delicious fare.
1181 Route 55, Lagrangeville NY; www.zoesicecreambarn.com

Enjoy our Bounty at Local Farm Markets
In your Dutchess County day trip travels, you’re more than likely to stumble upon farmstands that invite you to stop, sample, and stock up. If you don’t want to leave it to chance, we recommend putting Fishkill Farms or Barton Orchards on your itinerary, both of which offer markets full of fresh local fare and other on-site farm experiences.
Fishkill Farms: 9 Fishkill Farm Road, Hopewell Junction; www.fishkillfarms.com
Barton Orchards; 63 Apple Tree Lane, Poughquag; www.bartonorchards.com

Rock the Night Away: Daryl’s House Club
With its laid-back “hanging with friends” atmosphere, great food, and stellar live bands, this one-of-a-kind eatery and music venue is the perfect place to finish off your day in Dutchess. The club is brainchild of Rock & Roll Hall-Of-Famer Daryl Hall, who has personally overseen every detail, from the restoration of the historic building to the eclectic menu, which includes steaks, seafood, pasta, and a full bar. Some of the world’s greatest musicians perform intimate shows here, and tickets go fast, so book well in advance!
130 Route 22, Pawling; www.darylshouseclub.com

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