It’s party time in the Hudson Valley. In just a few days we’ll be hit with the Super Bowl, Mardi Gras and Valentine’s Day in rapid succession. You can find over 500 events in our calendar this week!
To help you navigate the many options, we’ve speared ten of the coolest Valentine’s Day events we could hit with our Cupid’s arrow of local love.
Love is unexpected
Rising Hudson Valley singer-songwriter Al Olender created Alentine’s Day “for the broken-hearted, the new relationship energy you don’t know where to put, the crushes you’ve had, for every shitty Valentine’s Day [she’s] had where the expectations were too high and the lows were too low.”
Instructions from Al herself: wear blue (the theme is “say I do with something blue”), arrive early at 6pm for delicious food by Camp Kingston, drinks by Darlings, and coffee by Velvet Moon. Vendors, merch, snacks, drinks and a photobooth will be set up before the show. Following the concert will be a Honeymoon themed After Party at Camp Kingston, the new cafe-bar on St. James Street. Special guests include Mikaela Davis, James Felice, Sage Horsey, Aubrey Haddard, Ross Newhouse, Jules Olson, Eion Falance, Tom Feeney, Amanda Brooklyn, Jesske Hume, Nick Kinsey and more. Dress your Valentine’s best and, in Olender’s own words, “get ready to have your world rocked.”
It all goes down on Fri. 2/19 at the Old Dutch Church in the historic Stockade District of Kingston.
When in Rome
Picture this: You’re just chilling in ancient Rome during the Festival of Love. Three goddesses have gathered to summon grooms for a young maiden. But something goes horribly wrong, and the grooms start dying. Jupiter and Cupid are there too. This isn’t a fever dream, it’s a Valentine’s Day themed murder mystery dinner by Theatre on the Road, held at Best Western in Kingston on Tue, 2/13 at 7pm. The troupe doesn’t disappoint, and “marriage can be murder” will no doubt be an unforgettable way to spend the day before Valentine’s.
Variety is the spice of love
Some of our area’s most entertaining characters take the stage at the “Laugh Til You Cry Valentine’s Day Variety Show” at Hutton Brickyards in Kingston on Wed. 2/14. The event, presented by O+, will be MC’d by the inimitable Isis Vermouth, who has been a part of some of the most legendary productions area partiers can hardly remember the day after. Amy G will merge comedy and cabaret for an unforgettably unique performance. Lauren Kincheloe will do standup. DJ E-Bomb will spin tunes, and various special guests will pop up throughout the night.
Heart and soul
For a jazzy, soulful evening of love and music, check out The Colony in Woodstock, which hosts Reggie Earls and Friends on Valentine’s Day. Earls returns to Colony’s stage after five years away in an hotly anticipated display of deeply moving musicianship. He’ll be joined by longtime friends and bandmates Matt Finck, Kyle Esposito, Dan Hickey and Keith Slattery, as well as some surprise guests like local pro jazz vocalist Lindsey Webster.
Live, laugh, love
Apologies for the cliche subhead, but if you’re feeling like you’d rather die, cry and withdraw this Valentine’s Day, consider getting a proper spirit lift at Laugh it Up Comedy Club in Poughkeepsie on Wed. 2/14. Not only will you get to guffaw at four of the area’s hottest standup comics, there will be a full dinner buffet with a dessert table and a champagne toast.
Honk if you’re…
Connor Kennedy set the VFW in Kingston on fire last year as the musical force behind a series of packed-house honky tonk nights. He returns this Valentine’s Day to host “The Honky Hearts Ball”. There’s a special vibe at the VFW honky tonks. It’s a super-inclusive and inviting scene, and feels like you’ve stumbled into an alternate reality where the oppression of modernity is left at the door and fun is all that matters. Not a bad way to spend your V-day.
Fun in the dark
Not into the saccharine pinks and purples of mainstream Valentine’s Day? Head to Graveside Variety in Woodstock on Wed. 2/14 for a “Gothic Hearts” dance party. The main attraction is an extended DJ set by Vudu Sister, a stunningly genre-breaking folk group that is influenced as much by Medieval and Victorian music as they are contemporary artists. Millions of Spotify streams are a testament to their unpredictably wide-reaching appeal. If “dark and unconventional” describe your dream evening, you won’t want to wake up from this dance party.
Love is far out
Froggy Daze knows how to throw a killer party. Organizers Peace Pad Productions are known for their legendary annual multi-day campout that’s drenched with hippie vibes, psychedelic lights, groovy bands and a general atmosphere of freedom and community togetherness. These legendary shindigs might have flown under your radar, as they often happen way out in the woods near Narrowsburg. This year, Peace Pad is putting on an epic Valentine’s Day party closer to us (but still deep in the woods), at the Hudson Valley Resort in Kerhonkson.
The 5th annual “Hoppy Valentines Masquerade Ball” stretches from Fri. 2/16 to Sat. 2/17, features two stages and two days of music, craft vendors, a diner pop-up, and, most romantic of all, an indoor heated pool. There’s a disco theme on Friday and a pirate theme on Saturday – you’re not going to find another Hudson Valley Valentine’s Day event that’s this far out.
Join the family! 
