- The Around the World Wine Tour is held every June.
Around the World Wine Tour
Held in June and sponsored by the Shawangunk Hudson Valley Wine Trail, this tasty tour affords "travelers" the chance to sample the culture and cuisine of countries from around the world, each paired with delicious local wines.
Pop, Rock, and Doo-Wop Series
Slated to run at Highland Town Field on Thursday evenings throughout July and August, this new live music series promises oldies and goodies from top local and national acts. Check the Town of Lloyd's website for scheduled performers.
Since the late 1800s, this old-time county fair in nearby New Paltz, which this years runs from July 31 through August 5, has been one of the Northeast's most beloved family outings. With rides, food, entertainment, vendors, horse shows, and more, it continues to draw attendees from all over.
Also held at the nearby Ulster County Fairgrounds, this year on August 18 and 19, this meat lover's summit adds live music and more to its chops-licking action, which sees culinary competitors vying for trophies and ribbons.
A picture-postcard helping of country Americana, this September 15 event at Gardiner's Majestic Field offers entertainment, games, food, and more family fun.
Prospect Hill Orchards Kids Days
Another all-ages pleaser, this two-day affair (September 24 and 25) at Milton's Prospect Hill Orchard boasts hayrides, face painting, cider pressing, and scarecrow building. On October 14 and 15, the farm hosts the Johnny Appleseed Cider Festival.
September 28 from 7 to 9pm is the only time the scenic Hudson Valley Rail Trail is open after dark. This annual, 2.5-mile round-trip, moonlit stroll includes a bonfire, a storyteller, doughnuts, popcorn, and cider. Bring a flashlight.
Santa Claus on the Walkway
Highland offers easy access to the breathtaking Walkway over the Hudson park/bridge, which from December 4 to 18 plays host to Saint Nick himself. Between noon and 2:30pm on Saturdays and Sundays, Santa can be found about halfway across.