5 Things to Do This Weekend: July 31–August 2, 2026 in New Paltz & Around Ulster County

The 6th Annual Draw-A-Thon

When: Saturday, August 1, 10am–10pm

Where: The Draw, 22 Iwo Jima Lane, Midtown Kingston

The Midtown Kingston Arts District is hosting its sixth annual Draw-A-Thon, and this year the event is expanding its reach. The Draw at 22 Iwo Jima Lane will be open for twelve hours straight, welcoming artists of all skill levels — yes, even if you're a complete beginner. No drawing skills required, which is exactly what makes this event so accessible.

Whether you want to spend a few hours sketching or commit to the full day, this is a chance to get creative in Midtown Kingston's growing arts district. The event is free to attend, making it one of the most budget-friendly weekend activities in the area.

More information: Visit midtownkingston.org

The Esopus: A History Presentation by Ulster County Historian Eddie Moran

When: Saturday, August 1, 12:00pm

Where: Historical Society of Woodstock, 20 Comeau Drive, Woodstock

Ulster County's indigenous inhabitants, the Esopus people, will be the focus of a presentation by County Historian Eddie Moran. Moran will trace the Esopus story from pre-colonial times through the American Revolution and into their forced relocation to Ontario, Canada, where their descendants remain today.

This is a rare opportunity to hear a comprehensive history of the people who called this land home long before European settlement. Moran is known for his detailed research and engaging presentation style, making this accessible whether you're a history buff or just curious about the land you live on.

Admission: Free

More information: Call (845) 679-2256 or visit historicalsocietyofwoodstock.org

Mid-Hudson Comic Con

When: Saturday–Sunday, August 1–2

Where: MJN Convention Center, 14 Civic Center Plaza, Poughkeepsie

If you're into comics, anime, gaming, or collectibles, the Mid-Hudson Comic Con is taking over the MJN Convention Center in downtown Poughkeepsie this weekend. This family-friendly event showcases artists, vendors, and a wide range of pop culture merchandise.

Convention Center Plaza is easily accessible from New Paltz (about a 30-minute drive north on Route 9 or the Thruway). Whether you're looking for rare comic books, anime figures, or just want to see the cosplay, this is one of the region's largest pop culture events of the summer.

More information: Visit midhudsoncomiccon.com

Orange County Fair (Final Weekend)

When: Through Sunday, August 2 (Weekend hours: 1pm–11pm)

Where: Orange County Fairgrounds, Middletown

The Orange County Fair is still running through this weekend, and if you haven't made it yet, Saturday and Sunday are your last chances. Weekend hours run from 1pm to 11pm, which is perfect for an afternoon-to-evening outing.

The 186th Orange County Fair features the traditional mix of agricultural exhibits, carnival rides, fair food, and live entertainment. This Saturday features Eyes of the Nile (an Iron Maiden tribute band) at 8pm on the Barn Stage, followed by a demolition derby at 7pm with gates opening at 5:30pm (additional tickets required).

The fair also has fireworks scheduled for tonight (Friday, July 31) at 9:30pm if you want to catch the finale.

More information: Visit orangecountyfair.com

General Richard Montgomery House Museum Open Day

When: Saturday, August 1, 2:00pm–4:00pm

Where: 77 Livingston Street, Rhinebeck

The General Richard Montgomery House Museum, part of the Rhinebeck Village Historic District and listed on the National Register of Historic Places, will be open for tours this Saturday afternoon. The house is maintained by the Chancellor Livingston Daughters of the American Revolution Chapter.

General Richard Montgomery was one of the first major generals of the Continental Army, killed in the Battle of Quebec in 1775. His house in Rhinebeck offers a glimpse into colonial-era life and the Revolutionary War history of the Hudson Valley.

This is one of several dates the museum is open this summer (also July 25, August 8, 15, and 22), so if you can't make it this weekend, there are more opportunities next month.

More information: The museum is part of the DAR chapter house at 77 Livingston St., Rhinebeck.

Plan Your Weekend

With the Ulster County Fair starting Tuesday, August 4th, this weekend is a good time to enjoy some of the area's other attractions before the fairground transforms for six days of agricultural competitions, rides, and concerts. Whether you're into art, history, comics, or county fairs, there's something happening within easy driving distance of New Paltz.