Orange County Family Weekend 10/8/26

Hi families,

This is one of those weekends when Orange County makes it easy to get outside. Sugar Loaf hosts a two-day fall festival, Warwick celebrates children’s books, and Mount Peter offers foliage views from the mountain. There are also two free picks and a bonus Monday option for families stretching the weekend through Columbus Day.

Here are this weekend’s best family picks, plus a rainy-day backup.

Saturday, October 10–Sunday, October 11 | 10 a.m.–5 p.m.
Sugar Loaf Arts & Crafts Village, Chester | Free admission

Spend the day exploring Sugar Loaf’s historic craft village, with artisan vendors, live music, food, drinks and family-friendly activities throughout the weekend. The village’s year-round studios and shops give this festival a more distinctive feel than a typical parking-lot event.

Good to know: Orange County’s Great American Yard Sale will also take place Saturday from 11 a.m. to 4 p.m. on the Sugar Loaf Performing Arts Center lawn, making it easy to visit both events in one trip.

Explore the Fall Festival

Sunday, October 11 | 11 a.m.–4 p.m.
Warwick Valley Middle School, 225 West Street | Free admission

Meet children’s and young-adult authors and illustrators, shop for signed books and enjoy crafts, read-to-the-dogs activities, a kids’ concert and food trucks. Admission is free, and the indoor location makes this one of the weekend’s strongest plans regardless of the weather.

Parent tip: Books and food are available for purchase, but there is no charge to enter. Ample on-site parking is listed, and no registration is required.

Meet the authors and see festival details

Sunday, October 11 | 11 a.m.–4 p.m. | Rain or shine
51 Old Mount Peter Road, Warwick | $20 per car

Spend Sunday on the mountain with scenic sky rides, fall foliage views, live music from Rock Slyde, food trucks, local vendors, a bounce house and pumpkin painting. Sky rides cost an additional $15 per rider or $10 for children ages 3–5.

Good to know: Bring lawn chairs or a blanket. Dogs, outside coolers, tents and grills are not permitted. Admission is payable by cash or Venmo, and there is no presale.

Plan your Mount Peter visit

Saturday, October 10 | 1–6 p.m.
Powerhouse Park, Tuxedo Park | Free admission

Tuxedo’s community fall festival offers live entertainment, food and family activities at Powerhouse Park. It is a good choice for families who want a local festival without committing to a full day or paying an entrance fee.

View the town event details

Saturday, October 10–Monday, October 12 | Check park hours before visiting
LEGOLAND New York Resort, Goshen | Included with park admission

Brick-or-Treat adds kid-friendly Halloween shows, LEGO builds, monster character meet-and-greets, a 4D movie and trick-or-treating at 10 candy stations beginning at 2 p.m. The activities are designed to be fun rather than scary, making this a strong choice for younger children.

Good to know: A dated ticket or eligible annual pass is required, and prices vary by date. Costumes are encouraged but not required. Check the operating calendar and current ticket price before purchasing.

Check tickets and event details

Saturday, October 10 | 10 a.m.–4 p.m.
240 Main Street, Goshen | $10 adults, $5 children ages 4–12

If the weather turns, explore the story of harness racing inside the sport’s historic Goshen home. The museum includes racing memorabilia, exhibits and interactive displays, and no advance reservation is listed for regular admission.

Planning note: The museum is closed Sunday and Monday, so keep this one specifically as a Saturday backup.

Check museum details

Monday, October 12 | 11 a.m.–3 p.m.
Pine Island | Check the event listing for final location and admission details

If your children are off Monday, Pumpkinfest adds a touch-a-tractor area, pumpkin painting, face painting, bouncy houses, games, food trucks and the event’s giant onion climbing net.

Check Pumpkinfest updates

Sunday has the weekend’s biggest concentration of events, including Sugar Loaf, the Warwick Children’s Book Festival and Mount Peter. If you want to avoid making a game-time decision, choose your Sunday priority now and use Saturday for Tuxedo, Sugar Loaf or the museum. Before heading out, check the official event link for weather-related changes, ticket availability and last-minute updates.

Have an Orange County family event we should consider? Send the official event link to [email protected] by Tuesday.

See you next Thursday,

Mickey
Orange County Family Weekend
Less searching. More family time.