How to spend Valentine's Day in the Catskills

Above: Miss Kitty's Saloon, one of the suites at the Roxbury Motel. Image via the Roxbury Motel website. 

According to legend, Saint Valentine was a pretty wild character who was incarcerated and executed for performing illegal marriages back in the third century, so there’s more to celebrate this Sunday, Feb. 14 than the memory of excruciating grade school card swaps.

So reclaim Valentine’s day from the mass-market chocolatiers and minions of mediocrity and celebrate his legacy of radical love with dining, partying, music and fun in the Catskills. Make a weekend of it: we’ve listed a few local hotels and inns that are running lovefest specials.


Leave ordinary reality behind and reserve yourselves a spot in one of the dreamlike themed rooms at the Roxbury Motel in Roxbury. The “Rad Romance” package includes flowers, champagne, cheese, couples’ massage, time in the Shimmer Spa and dinner at the Peekamoose Restaurant & Tap Room. And you’re minutes from skiing and boarding.

The drinks, of course, should be perfect. Nail it down by visiting Roxbury Wine and Spirits in Roxbury for a free Valentine’s Weekend Wine and Whiskey Tasting.  They’ll be pouring six wines and two whiskeys for your sampling delight on Friday, Feb. 12 from 4 p.m. until 7 p.m.

For a mouthwatering meal that you can relish in private, call ahead and reserve yourselves something from Ate.O.Ate Catering and Gourmet Food Truck. Pre-order by noon on Friday, Feb. 12 to get a Valentine’s Day feast delivered to your doorstep if you live in Roxbury, Arkville, Halcottsville, Margaretville or Fleischmanns.

Fuel up on pancakes, eggs, sausage and OJ at the Take your sweethearts to breakfast shindig being sponsored by the Rotarians at the Delhi firehouse. They’ll be serving from 8 a.m. until 12 p.m. on Saturday, Feb. 13.

Kick up your heels together to the sounds of Country Express at the Valentine’s Dance being held at the Delhi American Legion. Doors open at 6 p.m.; the band will play 7 p.m. until 10 p.m. on Saturday, Feb. 13.

Fall in love all over again on Main Street in Margaretville, where they’ll have fun going on all over town on Saturday, Feb. 13 beginning at 11 a.m. during Sweet on Main. Come in and meet the makers at Home Goods of Margaretville, taste sweet chocolate at the Catskill Mountain Artisan’s Guild, enjoy discounts and celebrations at the Cheese Barrel, Village Homemaker and Mountain Yarns. Feast with your honey at Summerfield’s and get a free rose and box of chocolates; wind up the evening at a “Mix, Mingle, Munch and Music” fundraiser that starts at 5 p.m. at Stick In The Mud.


At the Albergo Allegria (Italian for “Inn of Happiness”) in Windham, you can reserve a suite with a fireplace and a whirlpool, or just grab a room complete with a “dream-worthy” bed and a big HD flat screen. In the morning, they’ll serve you a delicious hot locavore breakfast.

Above: Couples renew their vows at Hunter Mountain. 

High on love? At Hunter Mountain Ski Resort in Hunter, any married couple that can ride or ski down the mountain can purchase a lift ticket or a season pass and join the group on the summit deck to renew their vows in a special ceremony scheduled for Sunday, Feb. 14 at 1 p.m. They’ll have a small reception afterwards at the Summit Lodge, after which there’s a group ski down the mountain. Van Winkle’s Restaurant will be serving up a V-day menu if you want to grab a bite before you go renew your honeymoon.


Celebrate Valentine’s Day with a spring house spa package at the American Hotel on Main Street in charming Sharon Springs. Stare into each other’s eyes in the cozy pub. You’ll get dinner and breakfast for two, a charming room, and your choice of Swedish or deep tissue massage.

There may still be time to grab a spot at the table for the Valentine’s Dinner at Heather Ridge Farm in Preston Hollow. The five-course dinner, limited to six couples, will feature the farm’s own grassfed beef filet mignon and other specialty items prepared by Chef Rob Handel. The dinner happens on Saturday, Feb. 13 at 6 p.m.; reservations are essential. The next day, the Bees Knees Café will be open from 11 a.m. to 3 p.m. with an a la carte brunch menu. Barista Robert Lugo, formerly the owner of Catskill’s Retriever Roasters café, will be brewing freshly roasted Fair Trade java to go with your mountain views from the 1820 farmhouse.

At Grapevine Farms in Cobleskill, they’ll be serving slow roasted prime rib or creamy chicken piccata by candlelight at 6 p.m. on Saturday, Feb 13. Reservations, please: 518-234-9148.

The Studio in Cobleskill is hosting a special couple’s edition Paint ’n Party night out. Your instructor will guide you step-by-step while you paint a beautiful painting. It’s happening Sunday Fen. 14 at 6 p.m.; admission includes wine and a light dinner.


At the Villa Roma Resort in Callicoon, boogie into the wee hours in the shimmering new Marty’s Lounge or beneath crystal chandeliers in the piano bar. Dip into the sauna and the indoor pool the next morning, and then sample dining choices that include an old fashioned ice cream parlor.

They’ll be dishing up a Valentine’s feast at Mr. Willy’s in Monticello from 5 p.m. until 10 p.m. on Saturday, Feb. 13, with treats like baked brie with raspberry sauce, seafood-stuffed rollatini and prime rib au jus. Reservations, please: 845-794-0888.

What’s nearly as romantic as a trip to Paris? A trip to the Valentine Cabaret at the Sullivan County Museum in Hurleyville.  Sullivan County’s finest voices will sing love songs and non-love songs at 8 p.m. on Friday, Feb. 12 and at 2 p.m. on Sunday, Feb. 14.

Above: Erine Harpe. 

Down at the Dancing Cat Saloon in Bethel, catch Erine Harpe performing “sexy soul and down home delta blues” on Saturday, Feb. 13 starting at 8:30 p.m. Friends or beaus welcome, they say; great food available too.

At Bernie’s Holiday Restaurant in Rock Hill, they’ll be serving “first kiss, second course, third course (intercourse), and the Happy Ending.” Don’t worry, they haven’t gone all Bunny Ranch--it’s their menu for a Valentine’s Feast that starts with Sweet Kiss martinis and continuing through steaks and lobster tails to your choice of three mouthwatering desserts. Serving throughout the day on Sunday, Feb. 14. Reservations recommended; call 645-796-3333.

Single in Sullivan this Valentine’s Day? Morgan Outdoors has a treat just for you. Join your fellow singles hiking on the Parksville Rail Trail, then warm up together over tapas and beverages at the Rolling River Café. It’s bound to be the beginning of some beautiful friendships. Hike steps off at 1:30 p.m. on Sunday, Feb. 14 They’re keeping the group to 15, so call 845-439-5507 to get your spot.


The Emerson Resort and Spa in Mount Tremper offers a selection of Royal, Regal and Imperial room s at the Inn, all of which feature 32-inch flatscreen televisions, gas fireplaces and oversized air jetted tubs. Dine in style at the Woodnotes Grille (they’ve got a special menu for Valentine’s Day), get a psychic reading, spoil yourselves at the spa, marvel at the psychedelia of the World’s Largest Kaleidoscope and shop the Country Stores.

Those in bah-humbug mode should not miss Love and Heartbreak: An Alt-Valentine Reading and Conversation at the Golden Notebook in Woodstock with Lisa Phillips, author of “Unrequited: The Thinking Woman’s Guide to Romantic Obsession” and Sara Eckel, author of “It’s Not You: 27 (Wrong) Reasons You’re Single.” Moderated by Chronogram books editor Nina Shengold, it’s happening at 4 p.m. on Saturday, Feb. 13.

Come to the Woodstock Library Forum for a rousing round of He Said/She Said with New York Times writer and young adult author Dakota Lane. Lane has been doing this Valentine’s performance for decades, differently every time but always fast, fun, and passionate. It’s happening on Saturday, Feb. 13 at 5 p.m., and includes “Valentines for all” and a five-minute writing class.

Another beloved Valentine’s tradition will be happening at the Rosendale Café in Rosendale: Amy and Leslie Valentine’s Concert, featuring the “unique and stellar” harmonies of standout homegirls Amy Fradon and Leslie Ritter, backed up by friends of equal stature on guitar, piano and drums. The music starts at 8 p.m. on Saturday, Feb. 13; get there early if you want to get a seat.

Come munch an exceptional brunch while luxuriating in the stylings of some great local vocals at the Valentine’s Day Singer Showcase Brunch at the High Falls Café in High Falls. They’ll be serving and singing from 12 p.m. until 3 p.m. on Sunday, Feb. 14. Reservations are required: 845-687-2699. 

Vine Van Gogh invites you to “Gogh together” at Novella’s in New Paltz, where they’re hosting a dinner buffet followed by a sip ‘n paint session. An amazing local artist will give you a step-by-step lesson on how to recreate two separate works of art that will go together as a unifying piece. Dinner is served starting at 5:30 on Sunday, Feb. 14.