The best things to do in Orange County

Osiris Country Club pairs Catskill views with a scenic course, a lively Tap Room, and a newly renovated Lakeview Ballroom for events. Between three golf simulators for rainy days, on-site cabins for quick getaways, and fresh 2025 membership options, it’s a solid home base for Walden golfers.

Whether you’re planning a barn wedding, a low-key family bash, or a corporate retreat that doesn’t feel like homework, Walden Riverside Farm brings four generations of Hudson Valley history with a hand-built Dutch barn, an 18th century farmhouse, fifty acres along the Wallkill River, plus optional drone video and…

From the Hudson Valley newsletter, October 20, 2026

Deep Roots Wrestling Club is a family owned and operated club giving local kids the chance to learn real wrestling skills and confidence that carries into school and life. If you want structure, solid technique and a supportive crew right here in the community, this is your room.

From the Walden newsletter, October 15, 2026

Whether you're sneaking in a quick game or rallying the crew for leagues and weekend bragging rights, Memory Lanes keeps it simple with open bowling, tournaments, and parties. Call ahead if you're timing-sensitive, then let the gutters have the drama while you chase that satisfying strike.

From the Port Jervis newsletter, October 8, 2026

Hickory Hill Golf Course has an 18-hole layout with four sets of tees, two putting greens you can chip on, and a grass-tee driving range, plus a fully stocked pro shop, lessons, junior camps, and the 19th Hole bar & restaurant for post-round debriefs.

From the Warwick newsletter, October 5, 2026

Warwick Drive-In Theater keeps the old-school magic alive with three big screens, fresh releases, and that cozy tailgate vibe you can't fake. Pack a blanket, cue the snacks, and enjoy a small-town tradition that still feels like the best night out in Warwick.

From the Warwick newsletter, October 21, 2026

W. Tillinghast’s 1915 pedigree in a playable 18 that still bites when you want it, especially on holes 2, 3, and 4. Tune up in the 19th Hole simulators, then refuel with brick oven pizza at The Lynx Tavern on The Green.

From the Port Jervis newsletter, October 2, 2026

Whether you're wrangling the kids, rallying a team, or chasing a new personal best, Pin Street at Warwick delivers 28 synthetic lanes with bumpers, a full service bar, arcade, billiards, and a pro shop. Family-owned, known for parties and leagues, and you can reserve a lane online.

From the Warwick newsletter, October 4, 2026

Alamo Farm Workers Community Center quietly does a lot: food pantry and clothing donations, a welcoming spot to relax and watch TV, plus ESL, homework help, and exercise classes.

From the Florida newsletter, October 1, 2026

Winding Hills Golf Club packs an 18-hole executive layout with plush fairways, water hazards, and Hudson Valley views that make a quick round feel like a mini vacation. Play a quick par-57 loop, then grab lunch by the waterfall and fire pit at The Venue, or rally the crew for an easy-to-run tournament.

From the Montgomery newsletter, September 30, 2026

Whether your kid is 15 months or a teen, Paradigm Athletic Center offers gymnastics, ninja, cheer, tumbling and even fencing right here in Florida, all taught with proper progressions and a yearly curriculum. Weekly open gyms, birthday parties and a team with State, Regional and National champions seal the deal.

From the Goshen newsletter, October 21, 2026

If you want relaxed, no-frills golf close to home, Scott's Corners Golf Course keeps it simple in the best way. A dependable spot for quick rounds after work, dialing in the wedge game, or introducing a buddy to golf without turning it into an all-day expedition.

From the Montgomery newsletter, October 15, 2026

Flagship Premium Cinemas - Chester keeps it simple with current Hollywood flicks in crisp 2D or eye-popping 3D, so you can skip the couch rut and catch something on a real screen. New releases, occasional throwbacks, and zero fuss make it an easy yes for a local evening.

From the Chester newsletter, October 13, 2026

When cabin fever hits or the kids need to burn energy, The Castle Fun Center comes through with laser tag, roller skating, bowling, arcade chaos, axe throwing, go karts, mini golf, even a rock wall. Perfect for birthdays, team nights, or spontaneous “let’s all do something” plans.

From the Chester newsletter, September 29, 2026

Skip the living-room scroll and head to Middletown Cinemas, a multiscreen spot with 3D showings and rotating new releases. They even host birthday party promotions, so you can celebrate between popcorn refills without trekking far from Goshen.

From the Goshen newsletter, October 9, 2026

Built in 1929 with famously great acoustics, Paramount Theatre in downtown Middletown mixes weekly film nights with legit live shows, from Dr. Temple Grandin on October 14 to The Spinners on November 7. It’s the kind of one-roof culture fix that makes weeknights feel special.

From the Port Jervis newsletter, October 14, 2026