May 2018 Upstate NY Events & Festivals | Fun Things to Do this Weekend in Ulster County

Posted by Dylan Taft on Thursday, May 3rd, 2018 at 4:04pm.

It’s beginning to finally feel like spring after what seemed like a never-ending winter! Trees are blossoming and the early spring tulips, daffodils and hyacinths are finally giving color to our yards after seeing so much of the white stuff for so long now. Here in the Hudson Valley, with the warmer weather, comes an abundance of events to give us a little break, keep our weekends busy and break us out of this past season’s extended winter hibernation.

Now that May has arrived, and with Memorial Day’s official kick-off of summer only a few short weeks away, there is plenty to fill our calendars with! Can’t forget that May 13th is Mother’s Day- but we’re covered there with some great events and things to do that Mom is sure to love too!

Ready to get out there and have some fun this weekend?

Check out some of our favorite local events happening this month!

May 4th & 5th- Women’s Woodstock Cycling Grand Prix

Benefiting the Boys and Girls Club of Ulster County and the Woodstock Fire Department, cyclists can enjoy a series of events taking place on Friday May 4th and Saturday May 5th throughout Phoenicia and Woodstock, leading up to the Rock City Road Race on Saturday morning. More course info and sign up can be found ➡️


May 4th-6th- Hudson Valley Tango Festival

A weekend long schedule packed full of workshops, lessons, conferences and seminars, taught by some of tango dancing’s biggest names. This year’s events take place in the popular Senate Garage in historic uptown Kingston, as well as throughout the Stockade District. Sign up and get more info ➡️

May 5th- Opening Day at Historic Huguenot Street

Now open for regularly scheduled tours for the 2018 season, Historic Huguenot Street will take you back in time to 1677 to see what life was like for the first European settlers of New Paltz. Tours, activities and other special programs will take place throughout the summer. For more information ➡️

May 6th- New Paltz Regatta

An annual New Paltz tradition, dating back to 1955, catch the parade of handcrafted boats and rafts (kicking off at 1:00pm) as they meander down Main Street and launch into the Wallkill River and race to the finish line.

May 12th- Rondout Waterfront Walking Tour

Join members of the Hudson River Maritime Museum as they explore the industrial and maritime heritage of the Rondout Creek in Kingston. Walking tour starts at 11:00 am and lasts about one hour, meeting in front of the museum. More details for this, and other scheduled walking tours ➡️

May 12th- Kaleidoscope Workshop at Emerson Resort and Spa

Both kids and adults alike can build their own kaleidoscopes with famed kaleidoscope artists, and learn about the history and science behind these fascinating viewfinders, all in the place that houses the World’s Largest Kaleidoscope, right here in Mount Tremper. More event details ➡️



May 13th- Eighth Annual Tulip Festival and Mother’s Day Celebration

Here’s one that Mom is sure to love! Spend the day at Honors Haven Resort & Spa in Ellenville, with a great collection of vendors to shop, entertainment and live music throughout the day, beautiful tulips and floristry to admire and a lunch buffet to top it all off. To make reservations ➡️


May 13th- Mimosas and Mother’s Day

Spend the afternoon at the base of the Shawangunk Mountains at New Paltz’s Robibero Vineyard. Relax with live music, wine tastings and of course mimosas, and to make things even better, the winery is pet-friendly, so Mom’s favorite four legged friend can come too! More at ➡️


May 19th- Rock the Ridge

Do you have what it takes to Rock the Ridge? This 50 mile endurance competition, ran over the course of 24 hours, will test runners of any skill level, in the beautifully picturesque Mohonk Preserve in Gardiner. Registration is required ➡️


May 19th- 10th Annual Cupcake Festival & 5K Cupcake Classic

Sweet lovers can’t get enough of the annual Cupcake Festival at Wrights Farm in Gardiner! Cupcake contests, food and craft vendors, raffles, bounce houses and other kids activities, wagon rides through the orchard and live music make for a great afternoon of sweet, sweet fun. Festival starts at 12:00pm. More info at ➡️  


May 19th- Hamlet of Highland Springfest

Highland’s annual spring street fair is back again, with more events than before. From 11:00am- 8:00pm, enjoy live music and craft and food vendors sprawled through the hamlet on Main Street. Throughout the day, numerous performances, demonstrations and games will take place, starting off with a Semper Fi 5K at 10:00am. Full list of events ➡️  

May 23rd-June 3rd- HITS on the Hudson Returns

From Wednesday-Sunday, starting on Wednesday, May 23rd, HITS on the Hudson Horse Shows return to Saugerties, for weekends I and II of their racing and jumping competitions. Family friendly fun to be had, and the equestrian world’s biggest stars. More info ➡️


May 26-28th- Woodstock-New Paltz Crafts Fair

It wouldn’t be Memorial Day weekend in New Paltz without the craft fair! Since 1982, the area’s largest crafts fair sets up at the Ulster County Fairgrounds for a weekend of shopping, demonstrations, food and live music. Fair information and admission prices ➡️

May 26th- Rail Explorers: Catskills Division

We can’t wait for opening day to get here so we can check out these cool Catskill pedal cars! From Phoenicia, follow the Esopus Creek on an 8 mile round trip electric pedal car ride for two. Trips need to be booked ahead of time online ➡️ 

May 26th- Step Into History Scavenger Hunt

This family friendly scavenger hunt winds through Uptown Kingston’s Stockade district, from 11:00am to 2:30pm. Guides can be picked up from participating stops, such as the Old Dutch Church, Senate House or Matthewis Persen House Museum in Kingston.

May 26th- “Great Train Robbery” on the Catskill Mountain Railroad

This interactive adventure takes you back in time to celebrate the legend of the 1903 silent movie, bearing the same name as the event. The trip kicks off in Kingston and travels through the Hurley flats, stopping at a local festival with live music, vendors and food. There will be multiple departure times and train tickets can be purchased online ➡️ 


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