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Article: Caroline's Country Guide To Upstate New York

Caroline's Country Guide To Upstate New York

Caroline's Country Guide To Upstate New York

Jeffrey and my six year (and counting) love affair with Upstate New York began the moment we bought our farm in the Hudson Valley. From the slower pace and changing seasons (hello, fall leaves), to the delicious restaurants and farm stands, this little slice of heaven has a plethora of hidden gems that we continue to discover. The fall season is just getting started here, which is one of the best times to visit and explore the area and the leaves changing colors, so I thought I’d put together a guide featuring our current favorite places to eat, stay, shop and play in Upstate New York…


Located in the heart of historic downtown Hudson, The Maker is an intimate hotel with 11 spacious rooms that are spread across three historic buildings. Each room is unique and has a story to tell… from The Artist Studio (see below), an ultimate bohemian refuge, to The Gardener, where wrought iron and soft furnishings meet flora art to create a lush, evocative space. They also have an amazing cocktail bar and lounge, which is tucked away inside a restored 19th century carriage house, with leather-clad walls, candle-lit corners and a hand carved fireplace.

The Maker, Hudson Valley

I can’t talk about where to stay without mentioning the magical Foxfire Mountain House, a vintage inn surrounded by woodlands and mountains in the Catskills. This 100-year-old inn has 11 guest rooms, a pond and lily pool, bonfire pits and a rustic outdoor pavilion made for dreamy fall evenings under the stars. Inside you can lounge by the stone fireplace on sheepskin rugs or on vintage velvet and leather sofas. Proprietors Tim Trojian and Eliza Clark spent three years renovating this historical space, from laying Moroccan tile to pouring a concrete bar, and it’s a true labor of love come to life. Read more about their design journey here!

Foxfire Mountain House, Upstate New York
Foxfire Mountain House


If there is one time of year to visit Upstate New York, it’s in the fall. The humidity has taken a back seat, a cool breeze has kicked in and the lush landscape has turned from green to various shades of yellow, orange and red – its fall at its absolute finest. One of my favorite spots to hike and see the fall leaves is Kaaterskill Falls. Nestled in the Great Northern Catskills is the highest cascading waterfall in New York State. Dropping in two tiers over 260 feet, Kaaterskill Falls is one of the region’s most popular destinations – it’s captivated poets, painters, filmmakers and photographers for centuries.


After a morning hike to the falls, our favorite spot to stop for lunch is Phoenicia Diner. Built in 1962, this old-style diner maintains its charm with an updated menu, focusing on fresh locally-sourced ingredients from Catskills and Hudson Valley farms. Enjoy traditional diner favorites with a modern twist, like pancakes, eggs benedict, avocado toast, sandwiches, burgers and a selection of hearty skillet dishes. Comfort food at its freshest, and finest.

Phoenicia Diner, Upstate New York


Where family friendly meets fine dining, Gaskins is a dining destination in the middle of our very own Germantown. Located inside a renovated historic grocery store built in 1890, Gaskins has an aesthetic that is casual, yet sophisticated. It blends in, yet stands out among the quaint architecture of the town, and each dish shines with fresh, locally-sourced ingredients. The seasonal menu changes daily so I can’t recommend a favorite dish, but I can guarantee that you won’t leave disappointed. 

Gaskins, Germantown, Upstate New York


Apple picking is a quintessential fall activity here in Upstate New York, and one I look forward to at the start of the season every year. Our favorite spot is Greig Farm, a fourth generation family-run farm in Red Hook, New York, a short drive from our house. The abundant “you pick” orchard has over ten different apple varieties – last year we left with 12 pounds of our favorite Gala apples that we used for baking and caning (see here). They also have a farm market, trails throughout the property, and my personal favorite, feeding the pygmy goats.

Greig Farm, Upstate New York


Among the historic brick buildings in Kingston, New York stands the blushed-hue exterior of Brunette wine bar. Located in the historic waterfront district, you simply can’t miss the pastel palette, and you won’t want to. Featuring a top notch selection of natural wines, beers and ciders, plus a casual, yet elegant atmosphere, Brunette is my go-to spot for a glass of wine. And if you’re in the mood for a bite to eat, their eclectic small plates can’t be beaten, like the trout roe nachos or chilled noodles.

Brunette Wine Bar, Kingston New York


Upstate New York is home to artisans, makers and craftsmen, and shopping their creations is a special, personalized experience that I love. One of my favorite spots to shop is Field + Supply, a modern makers craft fair that highlights goods, old and new – think handmade ceramics, furniture, textiles, leather goods and more. The fair is twice a year, with the second one on October 7th- 9th at the Hutton Brickyards in Kingston, New York. There will be over 200 vendors, plus a full weekend of live music, local eats and activities for the whole family.

Field + Supply, Upstate New York


If you’re looking to get your hands on all the fall harvest bounty, head to Montgomery Place Orchards Farmstand. It has an array of seasonal fruits, vegetables and other fare from 30 regional farms. The orchard was established in 1802 and is renowned for growing “antique” apples you may have never tasted. And don’t leave without trying their homemade Apple Cider Donuts and choosing from a variety of seasonal gourds and pumpkins.

Montgomery Place Farmstand, Upstate New York


The town of Tivoli is a short drive from our home and one of my favorite spots to grab dinner. When Jeffrey and I are in the mood for sushi we head to Osaka Tivoli, where the ingredients are fresh and made in house. Owners James Liu and his wife Joy took over the original restaurant in Rhinebeck after Joy’s father opened it over 25 years ago, bringing sushi to upstate. After much success, the family opened a second location in Tivoli, and we are so glad they did.

Osaka Sushi, Tivoli, New York


It’s not a visit to Tivoli without a stop at Fortunes Ice Cream. This cute little storefront was started by two Bard College grads who felt that Tivoli was missing a scoop shop. They serve up fresh, homemade seasonal ice cream using local ingredients - think Concord grape sherbet from Heller Farms in Germantown, and on my current list to try, the newly released Apple Cider Donut ice cream.

Fortunes Ice Cream, Tivoli


Explore the great outdoors through an artists lens at the Storm King Art Center. This 500-acre outdoor museum in the Hudson Valley allows visitors to experience large-scale sculpture under the open sky. The center aims to nurture the bond between art, nature and people by supporting artists and stewarding the landscape. Also a non-profit organization, it was founded in 1960 and each year continues to grow and evolve.

Storm King Art Center

When I first discovered Upstate New York, it reminded me of growing up in England, with the rich history and architecture, which I find myself gravitating to more and more these days. This area has become a big inspiration for me and I'm excited to share it with all of you. I hope you enjoy your time here, if and when you come for a visit. And let me know if you're looking for any other kind of recommendations!


Sending lots of love,
Photos courtesy (top to bottom): Caroline Diani, The Maker, Foxfire Mountain House, Fine Art America - Sean Mills, Phoenicia Diner, Gaskins, Caroline Diani, Domino, Hudson Valley Magazine, Caroline Diani, Visit Vortex Hudson Valley, Fortunes Ice Cream, Hudson Valley Happenings


Thank you for your thoughtful guide to Upstate NY! I was born in Pine Plains and am currently in Millbrook. I did venture out for a number of years but, moved back here to raise our kids. You gave me some new places to go, I bookmarked them and am eager to try.
oh, would you ever considered opening up a boutique around here? We certainly have nothing like it in the immediate area. Please ?!! ;)

Marcia Asplund

There’s just no better place to spend the fall the New England. I’m sure that upstate New York is right up there with Nantucket. I am here until October 14 and soaking up all the fall I can before going back to Southern California. I love shopping at Danny. My cousins live in Montecito so I’m probably there once or twice a year. Love your pictures

Vicki Livingstone

There’s just no better place to spend the fall the New England. I’m sure that upstate New York is right up there with Nantucket. I am here until October 14 and soaking up all the fall I can before going back to Southern California. I love shopping at Danny. My cousins live in Montecito so I’m probably there once or twice a year. Love your pictures

Vicki Livingstone

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