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  • Writer
  • Home Base: New York City
  • Weekend House: Pine Plains, NY

Karen Klopp is a co-founder of What2WearWhere.com, a blog that simplifies dressing for today’s busy women. “We take the guess work out of dressing, the legwork out of shopping, and the panic out of packing.” From the queries on the site came the book, “Packing for Travel, From Jet Set to Trek Set the Definitive Globe Trotting Guide”. Karen is a contributor to Huffington Post, Equestrian Lifestyle, and with her partner, Hilary Dick, writes a regular column for New York Social Diary. She resides in New York City and on a horse farm in the Millbrook countryside. With a backdrop of Manhattan and a background as a writer, documentary film producer, life-long conservationist, traveler, board member for various organizations, chair of countless events and wife and mother of three, Karen has participated in almost every kind of event that a woman experiences in her life. It’s with all this fabulous practice that she founded What2WearWhere to save today’s busy women their precious time by eliminating the stress of dressing for life’s events and travel!
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Karen’s shortlist for Upstate NY

"It is newly reopened by Cindy and Dan Kish to the delight of the local community. Early morning, you will see the horsey set, picking up breakfast before an early ride."


3 County Route 8 Ancramdale, NY 12503 - map  • 
(518) 329-5431

"It is a step back in time, with its admission honor system. The “zooies” from the school volunteer to help with the breeding and care of endangered species. You will never know what sort of wildlife you will come across there - over a hundred species."


282 Millbrook School Rd, Millbrook, NY 12545, USA - map  • 
(845) 677-3704

If we are feeling up for a little vigor, a hike up Stissing Mountain is on the agenda. There is access off of Route 82, turn west at the firehouse and follow the road around until you see a path and pull off for parking.   It is not a long hike and you are rewarded on top to a climb up the fire tower with 360 degree views the Berkshires to the east and the Catskills to the west. I have witnessed majestic bald eagles soaring below.


Instagram @Stissing Mountain

499 Lake Rd, Pine Plains, NY 12567 - map  • 
(518) 398-5069

Stissing House

Pine Plains, NY

"Michele and Patricia Jean’s cosy historic restaurant. Eat in the bar room and enjoy Chef Michele’s fabulous French inspired menu. Built in 1782 it has a illustrious and somewhat questionable past as an inn, tavern, restaurant and bawdy house!"


Instagram @Stissing House

7801 S Main St, Pine Plains, NY 12567, USA - map  • 
(518) 398-8800

"Stroll in the village of Millbrook and Franklin Street with its Saturday Farmer’s Market."


3263 Franklin Ave, Millbrook, NY 12545, USA - map  • 
(845) 337-1890

"Shop for dreamy wraps, throws and apparel at one of my favorite stores."


Instagram @aliciaadamsalpaca

3262 Franklin Ave, Millbrook, NY 12545, USA - map  • 
(845) 868-3366

"Here you will find the most marvelous gifts, fashion and one of a kind home goods."


Instagram @shop.punch.now

15 Merrit Ave, Millbrook, NY 12545, USA - map  • 
(845) 677-6796

"Feeling cultural? Pop into the Hamlet of Wassaic, where Wassaic Project has transformed old mill town into a vibrant and bustling artists’ community. With ever changing exhibits by artist-in-residence at Maxon Mills, your eyes and mind will be opened by the vast array of styles and subjects presented."


Instagram @wassaicproject

37 Furnace Bank Rd, Wassaic, NY 12592, USA - map  • 
(855) 927-7242

"Pop into the Lantern Inn for a cold brew at the bar, shooting darts and billiards while hanging with the local crowd - boho Brooklyn meets country life. Not to be missed!"


Instagram @wassaiclantern

10 Main St, Wassaic, NY 12592, USA - map  • 
(845) 373-8389

"Troutbeck is a 1765 country inn and tavern lovingly restored by new owners. Nestled in a park-like setting, it boasts a rich history of guests seeking a country retreat, and captures the spirit of the like of Mark Twain, Henry David Thoreau, Ralph Waldo Emerson and the naturalist, John Burroughs. Take time for a cocktail as you wander the first floor public spaces and marvel at the inspired decor that amalgamates the historic past with a modern flair."


Instagram @troutbeck.ny

515 Leedsville Rd, Amenia, NY 12501, USA - map  • 
(845) 789-1555

"The Rail Trail runs from Amenia to Millerton and is a wonderful way to see the topography of the area while working off calories for lunch in the town."


Harlem Valley Rail Trail, New York - map  • 
(518) 789-9591

Hunter Bee

Millerton, NY

"One of my favorite antique stores on Main Street."


Instagram @hunterbeeshop

21 Main St, Millerton, NY 12546, USA - map  • 
(518) 789-2127

"Great antiques shop on Main Street in Millerton."


Instagram @montageantiques

25 Main St, Millerton, NY 12546, USA - map  • 
(860) 485-3887

"Always chock full of fun finds!"


Instagram @millertonantiques

25 Main St, Millerton, NY 12546, USA - map  • 
(518) 789-6004

"Don’t leave without a pop in to Terni’s Dry Goods Store, family owned and operated since 1919.  It is a treasure trove of practical and beautiful things."


Facebook @Ternis

42 Main St, Millerton, NY 12546, USA - map  • 
(518) 789-3474

Harney & Sons

Millerton, NY

"Harney’s Tea Room is a quiet place to re-energize."


13 Main St, Millerton, NY 12546, USA - map  • 
(518) 789-2121

"Hudson, NY is a bustling area of antique and mid-century shops and restaurants. Plan the trip when the John Stair Gallery is holding one of its superb auctions."


Instagram @stairgalleries

549 Warren St, Hudson, NY 12534, USA - map  • 
(518) 751-1000

"Walkway Over the Hudson is on my bucket list. I plan to take it on this summer and instinct tells me that early morning would be the best time to enjoy the majestic spectacle of the mighty river."


87 Haviland Rd, Highland, NY 12528, USA - map  • 
(845) 834-2867