This Weekend: Valentine's Day in the Catskills

Above: Snowmen in love in Roxbury promote Sunday's Hearts in the Hamlet event, via Facebook.

Just when we desperately need a celebration to take the edge off the cabin fever and the late-winter blahs, here it is Valentine’s Day. What could be lovelier? In the Catskills, love is something that’s celebrated year round, but this weekend it’s the star of the show. Come out and create and play and feast and dance. All events are happening on Valentine's Day itself -- Saturday, Feb. 14 -- unless otherwise indicated. 


Margaretville and Roxbury have teamed up to boldly claim this holiday as a signature festival, and they’ve set a grand buffet of love-themed fun for you and yours to feast on. Local shoppers and diners at a long list of participating businesses will be given “Spread the Love” heart-shaped guitar picks (you can get those any day from now through Feb. 16) that can be redeemed for special discounts; that purchase gets you yet another heart-shaped pick.  But the shop=local love is just the beginning of a festive weekend.

In Margaretville, on Feb. 14 from 11 a.m to 4 p.m., it’ll be Sweet On Main as local merchants and organizations treat you to samples and tastings of chocolate, cheeses, and fine wines. They’ll have a lot of free, love-themed kids’ activities and crafts. Besides Silly Selfie stations set up all over town to memorialize the occasion, there will be an awesome selection of photo props (and maybe some drama coaching) offered by Open Eye Theater. Oh, and the Watershed Post folks will help you craft a Laughable Love Letter…and you know we’re funny, funny people.

On Sunday, Feb. 15, it’s on in Roxbury, as Hearts In The Hamlet fills the street with delights. The Roxbury Arts Group offers kids’ crafts starting at 11 a.m., as well as the opportunity to get a photo or poem created by pros who will use the raw material you offer to personalize it just for you. Between 1 p.m. and 4 p.m. you can take a ride in a red velvet horse-drawn surrey. (If you reserve in advance, you’ll get all the trimmings: poem, pic, wine, and chocolate.) There will be tastings a-plenty, and a pop-up café with live music and the Ate.O.Ate food truck.

In Margaretville and Hobart, strap on your snowshoes and for the January February March, two self-guided, interactive audio walks through the woods and the hidden corners of town. 

Thinking about celebrating in your own cozy love den? Get your romantic essentials together at the Greater Stamford Area Chamber of Commerce pop-up farmers’ market happening Friday, Feb. 13 from 3:30 p.m to 6 p.m. at the Churchill Gym in Stamford. Baked goods, fresh local wares, gifts, books … you can even get your nails done special.

The enchanters of Ate.O.Ate Catering will be at that market, and at Sunday’s pop-up café in Roxbury. But if you don’t want to budge even that far, they’ll bring you a catered feast from their special Valentine’s Day menu. (Order by today, Feb. 12.)

In the mood for a dinner dance? The folks at the Castle on the Delaware in Walton have you covered. There’ll be a lavish feast served starting at 8 p.m. on Saturday, Feb. 14 for just $20, or you can pay just $5 to boogie down with Ernie Kinch and Joint Effort. 


Ain’t no mountain high enough? Think again. Married couples with lift tickets or season passes are invited to renew their vows atop Hunter Mountain on V-Day on the Summit Deck with Reverend Karen Monk of the Kaaterskill United Methodist Church. After your celebratory journey back down the mountain (ski or ride) they’re throwing a reception party in the Summer Lounge.

Love’s about making beauty together. Do it the fun way, with hammers and chisels and chainsaws. Bring the people you adore and make something hard and shiny at the Ice Sculpture Festival being held in Tannersville. On Saturday, Feb. 14 between 10 a.m. and 3 pm., talk to Karen at Maggie’s Crooked Café and she’ll direct you to your ice block.

Below: Ice carving in Tannersville. Via the Great Northern Catskills website. 

On Saturday, Feb. 14, you can head up the hill to the Deer Mountain Inn near Tannersville and soak up the sweet, sultry sounds of the American Songbook at a classic cabaret sponsored by 23Arts Initiative. Featured at the Valentine's Cabaret Jazz: A Tribute to the Great American Songbook will be the  Marion Cowings, trio: Cowings on vocals, pianist Eli Yamin, and bassist Mary Ann McSweeney. The show starts at 8:30 p.m.. Reservations are required; call 518-589-6268.


There’s no love like the love of a rescued pet. Get your furry love and sweet treats at the Schoharie Animal Shelter’s Valentine’s Day Bake Sale and Adoption Clinic. They’ll be at Tractor Supply in Cobleskill from 10 a.m. Saturday, Feb. 14 until they run out of goodies, so go early.

Above: Poster for My Funny Valentine in Schoharie County, via the Apple Barrel Facebook page. 

Laughing together is the best medicine, even if you’re not ailing. So come out to the Apple Barrel Country Store Café in Schoharie for My Funny Valentine, happening on Friday and Saturday night with four dinner seatings each evening. Feast on a celebratory menu and laugh it up with Friars’ Club comedian Greg Aidala. Call 518-295-7179 for reservations.


Warm feelings and good coffee will flow at Love Songs Through The Ages, a cabaret-style feast of songs from the 40’s on down, happening Friday, Feb. 13 and Saturday, Feb. 14 at 8 p.m. with a 2 p.m. matinee on Sunday, Feb. 15. It’s being hosted by the award-winning folk of the Sullivan County Dramatic Workshop at their winter digs, Sullivan County Arts and Culture Center in Hurleyville.

Opera lovers will converge for a Valentine’s Day double shot as SUNY Sullivan in Loch Sheldrake presents The Met Live In HD, with the enchanting fairy tale "Iolanta" to be followed up by the erotic psychological thriller "Bluebeard’s Castle." Show time is 12:30 p.m. on Saturday, Feb. 14 in the Seelig Theatre in Loch Sheldrake.

Do your Saturday, Feb. 14 evening wooing, wining and dining over a special dinner and music at Dead End Café in Parksville. Terri Hall on vocals, backed up by Larry Ravdin on saxophone, are headlining; you’ll also hear host Tom Caltabellata with Barry on keyboard. Dinner starts at 5 p.m., music at 6 p.m.

Above: Where to find free cake in Jeffersonville this weekend, to celebrate WJFF's 25th birthday.  

Your loving hearts will shine a light on the entire community of Jeffersonville after you partake of the JEMS Valentine’s Dance; proceeds will benefit the town’s beautification. Besides that, you’ll have great food and music at Mullally’s Pub. Mystic Entertainment is bringing the tunes, and there will be a 25th anniversary celebration of radio station WJFF 90.5 FM thrown in, with cake being served throughout town to celebrate. It’s happening Saturday, Feb. 14 starting at 7:30 p.m.

The Sullivan Hotel in Rock Hill is offering a spoil-yourselves-rotten Saturday night with cocktail hour, gourmet dinner and dessert (a white chocolate fountain, no less), dancing to the sounds of partymaster DJs, and a long-stemmed rose. The festivities run from 7 p.m. to 11 p.m.; you can add on a room and let the champagne flow.


Single skiers and snowboarders (and those who desire them), this one’s for you. Belleayre Mountain in Highmount is offering speed dating, also known as Lovers’ Lane on the Super Chief lift. Register between 11:30 a.m. and 12:30 p.m. for the fun that runs from 1 p.m. to 3 p.m. on Saturday, Feb. 14. You can ski some more and then get to know each other during the President’s Style Torchlight Bash from 5 p.m to 9:30 p.m., featuring the sounds of the Flying Turtles.

Feeling like something a bit more sedentary? At the Emerson Resort and Spa in Mount Tremper, you can check yourselves in for the Couples’ VIP Treatment any time during February: a rose petal bath with sparkling beverage and chocolate-covered strawberries, followed up by a 50-minute side-by-side massage and a trip to the steam room, sauna, and/or outdoor Jacuzzi. On V-day, you can get a psychic reading and the Country Store will offer Valentine-wrapped specialty chocolates.

Saturday night, Feb. 14, catch the hard-chargin’ bluegrass outfit Town Mountain in a special Valentine’s visit to the Rosendale Café in Rosendale. Feast on gourmet vegetarian for dinner first, or just come hear the band at 8 p.m.

Over at the High Falls Café in High Falls on Feb. 14, they’ll be partyin’ down with a Soul City Motown Review St. Valentine’s Day Dance Party. Ain’t no mountain high enough to make three hot lead vocalists backed by a four-piece rhythm section anything less than worthwhile.

Above: The Valentines Ball with the Marc Black Band, via the Bearsville Theater website. 

Up at the Bearsville Theater in Woodstock on V-Day, they’re having a Valentines Ball with the Marc Black Band, featuring Amy Fradon, Warren Bernhardt, Eric Parker and Michael Esposito. Black was recently inducted into the New York Chapter of the Blues Hall of Fame, and will no doubt be feelin’ the joy as the MC. You can count on an evening that’s “all about laughter, song, groove… and love.” Showtime is 8 p.m.

And down in New Paltz, at Unison Learning Center, they’re kickin’ out the jams with a Valentine’s Day dance powered by premier Hudson Valley party band Soul Purpose. They mix the soul, blues, swing, Motown and jazz sounds into a concoction that’ll keep you on your feet.

For more Valentine's Day weekend events in the Catskills, or to add your own, check out our self-serve events calendar.