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GUIDE to Roxbury, NY:

Updated: Aug 6, 2021

Things to see, eat and enjoy…some you gotta’ try and some are let’s just say – magical!

All right HVHer’s, it’s time to grab your please-don’t-over-pack weekenders and head north to the historic area of Roxbury. Now, I know some of you are giggling to yourselves, “Roxbury? One night!” Actually, it was four and not at an 80’s movie nightclub. Although parts of the area could be considered a touch psychedelic or neon in nature (more on this in a bit), the upstate New York neighborhood is a hamlet going through a transformative renaissance you’ll want to be a part of.

Roxbury, NY is about a three-hour drive from New York City toward the eastern edge of Delaware County in the Catskills. At first, you might think to your I-don’t-drive-more-than-two-hours-out-of-the-city self… “three hours? No way…not me!” But this is one trip worth a Cinderella-Cinderfella whirl. A straight-up ride on the thruway, along picturesque woods, beside crystal-clear streams, near rushing riverways, and up over some of the most beloved mountain views…it’s truly one freakin’ beautiful sight to behold as you make your way from the concrete jungle to the fresh greens and wild florals of the small historically preserved maple-lined community. Its car views are sure to fill every mother-nature-lovin’ soul!

If you frequently follow Team HVH, you know we work tirelessly scopin’ out and unearthin’ some of Hudson Valley’s most incredible hidden gems to share with ya’ll and this getaway guide is no different…or is it? Hmmmmmm? Ya’, fowa shuwa, we popped in and “shopped til we dropped” at one of Roxbury’s most unique, locally supported farmer’s market Pakatakan. We checked out one of the area’s newest arrivals the Fierce Grizzly - a specialty grocery and bistro of the adorable kind. We partook in some “food/cocktail porn” thought up, whipped up, and served up by some of the area’s best at Tito Bandito's, Binnekill Tavern, and ateOate at Shephard Hills…our tums are still recovering. Yup, all the types you rely on us to uncover for you…we found. Hold up though! There’s more to this fairytale adventure. This time, in addition to what you crave for us to reveal and share, we’ve pulled back the curtains on the area’s most one-of-a-kind experience, the crown jewel of our four-day getaway, a magical labor of love – The Roxbury Experience! Yeek, we’re jumping out of our ever-lovin’ creative skins!


First though, let’s get packed…


Pack or pick up on the way

  • A touch of slurpy neon lime green – t-shirt, flip-flops, hair scrunch, mani/pedi, dress, or swimsuit/trunks…I promise, this will make your respite more fun!

  • Themed attire (optional) – this will make sense shortly

  • Mobile charger – You won’t want to miss a single moment…post, share, stories!

  • Good walking shoes – for sights that require a closer look (waterfall alert!)

  • Sunscreen & Sunglasses – lots to do and see outside

  • Extra natural bug spray – It’s the country people… bugs live here!

  • Over-sized tote – doubles as a pool bag and to hold your local purchases

  • Patience – Mobile service is limited…you’re on vacay, aren’t you?!


Here’s HVH’s four-day itinerary and further down all the ooey gooey details. As always, you are welcome to “copy paste”, go with the flow, or for you planners, strategically plot and pin. Whatever your preference, our goal is always to inspire you to be in the moment, explore our local towns, cities, villages in and around the Valley, and most importantly, make memories you will want to share and remember for a lifetime. Or at least until we give you another locale to obsess over!



The Roxbury at Stratton Falls…are ya’ ready? Grab your neon lime green gear (or Aperol-orange tones can work in a pinch too) and here we gooooooo!

Gregory (Greg) Henderson and Joseph (Joe) Massa are the proud, talented owners and creators of the area’s most extraordinary, fun stay place, The Roxbury at Stratton Falls. If you haven’t been yet, then prepare for some real FOMO as we give you the deets (more than usual, but impossible to capture everything) that make their story book (even film-like) contemporary lodging unlike any other.

Let’s start with our arrival. As we made our way down the where-the-heck-are-we country road, we couldn’t help but gasp as we came upon the stately, fantastical, black, white, hint-of- neon-lime-green property…it is a showstopper! No seriously, the attention to details (like their newly perfectly placed antique gargoyles at the property entrance…hummm, I wonder, do they have names?) is mind-blowing…an insta-dream. From the eight themed tower cottages to the proudly standing Italianate Mansion (seven add’l themed rooms), The Roxbury is a sight to behold at every turn…and team HVH stayed for four glorious pinch-us-are-we-dreaming stayovers – a different cottage each night! Ask us which was our favorite and each of us will probably tell you something different…there’s somethin’ for everyone and I mean everyone…darn it…bring the whole family…or at least your besties!

Enter stage right…the fore mentioned optional themed attire. Ever contemplated what it’s like to wear a glass slipper? What about aliens, superheroes, fairies, dragons, Draculas and mythical gods and goddesses? I could go on and on – this place begs you to leave your ho-hum basic behind, dream a bit, escape your day-to-day…seriously, just have fun and soak in all the magical possibilities! God only knows, we all need it.

Want a further look into the Roxbury Hotel? Click here for our full Youtube Video

GOTTA’ TRY – A little that way…no, this way. It’s a bit crooked, no? It is! Inspired by a stretched-out version of the Mansion, Crooked Cabana is a must-do, gotta-try. Whether you’re a hot tub lovin’, sun soaker, sauna sweater, water dippin’, or any-hour-happy-hour kinda person, the Cabana is not to be missed. Be sure to order up one of their newest adult bevs – Cinderella Dressed in Yella! Oh, chaaaaarming! The crew would love anotha’ please!

FUN TO KNOW – The Roxbury team has a bit of a sweet tooth. I nearly died when I was greeted by dishes and bowls of sugary surprises and delights purposefully placed around their regal looking turquoise and gold lobby. Sweeeeeet!

THERE’S MORE – Definitely so much more (like their original lodge just down the road). But I think I saved the best or should I say…the most heartfelt for last. I’m told that when Greg and Joe uncovered what is now the trail of waterways and waterfalls that grace the Stratton property, they couldn’t help but think, “If fairies do exist then this is where they would live.” And so, began the adventure



Tito Bandito's…and après ski? What? Why not! Just a hop, skip, and a stone’s throw away from the local ski resort and about 20-ish minutes from the Roxbury Experience, this taco and tequila bar serves up tum-lovin’ fresh Mexican plates every TGIF through Sunday. We popped over mid-day and enjoyed a variety of south-of-the-border-inspired delights. Top of the list?...Baja Fish Tacos! Its slightly spicy yum-creamy radish slaw was a memorable bite full whipped up by Chef Laurie Merwin. This is no out-of-the-jar-joint. All their salsas and sauces are house-made! Before leaving, the sweet tooths of the group…well, they devoured the Tres Leche and the cinnamony, sugary coated Churros…si, mucho bueno!

Wait a sec! Who “dat” behind the bar? It’s none other than one of New York’s finest, Chef Owner Bryan Calvert. Once calling Brooklyn his home base, he now lives in the Catskills serving Tito Bandito's delights with business partners, Philip Faranacci and Peter Botros, inspired by tradition and made with some locally grown.

GOTTA’ TRY – Just one word…M-A-R-G-A-R-I-T-A-A-A-A-S! On the enthusiastic reco of a welcoming local, we opted out of our classic-salt-rimmed-rita box and tried our hand at one of Tito’s seasonal concoctions…the Watermelon and the Blackberry Hibiscus. Mixologist, Krista McCardle, muddled, shook, and rimmed up a mind-blowing bev to add to our gotta's try margarita tour list – olé!

FUN TO KNOW – From the street view, Tito’s may look slightly unassuming, but inside there’s a fiesta goin’ on! Decorated in authentic Mexican trinkets, oil cloths, sombreros, designer-friend Linda Keil coated the inside of Tito’s with a healthy dose of “Day of the Dead” including resident insta-star...their very own “Catrina.”

THERE’S MORE – Tito? Like the vodka? No, no, no! Well-named after the owner’s Pomeranian... apparently notoriously known for stealing socks!


Binnekill Tavern…Benny killed who? Sorry, couldn’t help myself! I’ll explain the mysterious name in a bit, but what you might not know is Binnekill Tavern is the “sister” of Tito Bandito's. Hudson Valley Happenings had the pleasure of dining at the second restaurant of Chef Owner Bryan Calvert’s, and partners Philip and Peter, during our 4-day stay at the Roxbury Experience. Slightly closer to the “inn”, the quintessential mountain tavern is most known for its rustic prepared types. Chef describes it as food with a “sense of place.” It was fascinating sitting for a bit and chitty chatting about his journey from Brooklyn to the Catskills (He’s quite the history buff and knows a lot about the area he now calls home.) …you know, given his acclaim and all.

Chef Calvert introduced us to several hearty, yet delicately prepared dishes by Chef de Cuisine, Nicole Haroldsen. One by one, each dish arrived artfully plated…some savory and others varied in bright vegetable tones. Amongst us (meaning team HVH) it was a toss-up between the Catskill Smoked Trout Salad and the Roast Lamb Sirloin. My vote (and I am no food critic by any means) was definitely the Smoked Trout Salad - loved it!

GOTTA’ TRY – No joke…the skillfully crafted smoked cocktails by Mixologist, Dennis Gleen, were a-m-a-z-i-n-g! Wood-made smoke is first captured inside a capped carafe filled with a splash of this and that of Dennis’ liking, let to stand for a wee bit to absorb the smoky flavor, and finally released into a rocks glass …ahhhhh…heaven! These are more than just a gotta-try…they are a must-try!!!

FUN TO KNOW – Ok back to "Binnekill". Dutch in origin and specific to the Catskills, means the backwater portion of a stream or the remnant of an old stream bed. There ya’ go…and yes, the tavern is located above a stream bed.

THERE’S MORE – Want to cook like a chef…or at least try? You can pick up Chef’s book, Brooklyn Rustic while dining at Binnekill Tavern. We were lucky enough to score one!


ateOate…or 808? I’ll circle back on this in a min. The Roxbury fav is a tavern-styled eatery located on the sprawling country-tucked-away golf course at Shepard Hills. It’s kinda, sorta not easy to find but locals know it! I was a bit lost trying to catch up with the gang for a bite when I had to ask a local for directions, “Oh, ateOate? That’s some gooood food!” was the first thing out of her mouth…I’d say that’s an unsolicited 5-star review!

Chef Rich Ellsworth (so posh sounding, no?) is self-taught and has very unusual takes on some pub classics…like the explode-in-your-mouth Ruben Fritters! Ah-ya!

We went crazy for them…how did he do it?!

Our creative guru at HVH is Hawaiian-born and noticed a touch of her beloved state present in some of the dishes we scarfed down. After a bit of probing, come to find, Chef Ellsworth and his wife love Hawaii and find the essence of the islands to be quite special (aloha!) So, each time they visit, the chef brings back a new recipe to recreate home and add to the menu – with his twist on it of course.

GOTTA’ TRY – This is a no brainer – 808 Maui Pork Belly and yup, you figured it out the Ruben Fritters. If you like Pork Belly this is no doubt a gotta-try for you. Its hints of the magical Pacific Island puts this dish into a whole new category – we promise!

FUN TO KNOW – So, now to answer the question, “Where does the ateOate come from?” When Chef and his wife were starting their business, they were searching for the perfect name. At that moment, their clock read “808” …it was kismet…”808” is the area code foooor – can you guess? HAWAII! They played a bit with the spelling and as his wife shared with me, the rest is history!

THERE’S MORE – Just a fun fact, Chef’s new pup is named, “Maui!”



The Fierce one of Roxbury’s newest kids on the block. The specialty grocery and bistro literally opened its Route-30 doors (53530 to be exact) for business within days of our jaunt to the upstate hamlet. Located directly on the main street center, this petite in-town-oasis of necessities and goodies (attention, attention apple cider donuts!) is run by a husband-and-wife team. Needing a few things to carry us through our stay, we figured it would be a good “idear” to check out the neighborhood newbie. And, given The Roxbury at Stratton Falls didn’t serve food (although plenty of snacks for purchase), The Fierce Grizzly seemed to fill our order for a quick casual bite too.

Stocked to the gills with Roxbury-made/Catskill-made/New York-made, this charmer is quite the purveyor.

From locally bottled milk to just-picked organic sweetly bundled herbs (loved it!), to crispy edged breads and deliciously aged cheeses, this one to watch!

GOTTA’ TRY – Most definitely, their pressed sandwiches. On the day of our visit, they were serving a layered creation of tasty melted specialty cheese, caramelized onion, and pesto – oh yeah, it stopped my hangry stomach from grumbling!

FUN TO KNOW – Who’s that doggy on the store front? Did ya’ see them? Those bright bubble gum pink Schnauzer silhouettes. Could it be? No? Oh, it most certainly is - pink pooches by none other than famed NYC graffiti artist Peter Mayer! I hear he pretty much drops in daily for a nosh at the new spot. Johnathon Beck, the owner, commissioned Peter to tag his grocery front with the infamous pups.

THERE’S MORE – Although The Fierce Grizzly is an eclectic assortment of items, by design and desire, it’s community-friendly and affordable.


Pakatakan Farmers’ Market…is more than a collection of organic vegetable growers. It appeared to us to be a carefully thought-out assembly of the unusual and the all-important farm grown, farm raised staples gathered under one country sky roof. From bright and fragrant garden bedding plants and award-winning sprits to handmade soaps and moon infused elixirs, delectable soups and maple infused everything, locally fermented Kimchi, and straight-out-of-the-water fish…this was one market reminiscent of those I’ve come to know in Europe.

GOTTA’ TRY – Honestly, there were so many “gotta-tries’ but on the tippy tippy top – the Belgium Waffles from Pikas Farm Table were a salty-sweet combo of heaven, the give-me-peace-of-mind teas, tinctures, and salves infused with goodness of specific moon phases from Elder Sisters Apothecary were a selfcare must, and the kitchen made deliciously smelling soaps from Locust Grove Soaps were perfect take homes.

FUN TO KNOW – The 128-year-old completely round barn structure is the focal point of the market. Rich in local family history, it is one of the only round barns still standing in good condition and operating today…wow, that’s some strong bones!

THERE’S MORE – Impossible to capture all the community-created worth sharing in this guide; be sure to pop by or look up these gotta-tries too: Mulligan Creek Acres, Skytop Springs Fish Farm, Neil Powell Studio, East Branch Farms, Shaver Hill Farm, Kerrs Creek Distillery, and Union Grove Distillery.

Roxbury, New York you sure have a lot to share. Thank you for sprinkling us with your magical fairy dust and showing us why “you” need to be on our must-visit list!

Xo jojo


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