From Driving Range to Dream Courses: Country Clubs I'm Eyeing Around Bedford and Beyond
When I moved up to Bedford from Brooklyn with my son, we had two goals in mind: more space, and more swings. Not the playground kind—though we still hit those too—but golf swings.
Truth is, I’ve casually golfed since I was a kid. My dad played, so I played, kind of. But it never quite stuck. Then the pandemic hit, and like a lot of parents, I found myself trying to create structure, fun, and sanity—often all at once. My son picked up his plastic clubs, and before long, the driving range became our second home.
What started as a way to get out of the house turned into something more. Now, golf is a ritual. A laugh. A reset. And while I’m far from scratch (laughably far, some days), I’ve come to genuinely love this game—and the community around it.
So, I figured it’s time to share the local country clubs that are on my radar. I’m not a member of all these (yet), but if you’re new to the Bedford or Westchester area—or just thinking about it—these are five standout clubs worth knowing.
There are plenty more worth exploring, too—so if I missed your favorite, let me know what should be on my list next.
1. Sleepy Hollow Country Club – Scarborough
Let’s start with the dream. Sleepy Hollow isn’t just a course—it’s a postcard. Perched above the Hudson River, the views are unreal, and the course consistently ranks among the best in the country. The clubhouse? A literal Vanderbilt mansion. The pro shop merch? Irresistible.
Yes, membership is exclusive. No, I’m not there (yet). But if you’re after old-world grandeur with a side of elite golf, this is the one to fantasize about.
2. Westchester Country Club – Rye
If Sleepy Hollow is the dream, Westchester Country Club is the institution. With two 18-hole courses, a huge tennis program, pools, and events galore, it’s practically a resort. It’s hosted PGA events and holds some serious history—Gene Sarazen once won a championship here and got his appendix removed right after.
Family-friendly, legacy-driven, and buzzing with energy, it’s the kind of place where golf is just the beginning.
3. Knollwood Country Club – Elmsford
Here’s a classic that keeps it real. Knollwood is one of the oldest country clubs in the U.S., but it doesn’t carry the pretense you might expect. It’s known for being accessible, with recently updated facilities, a great pool scene, and even bocce (which is way more fun than I thought it’d be).
For anyone looking to ease into country club life without six-figure sticker shock, Knollwood is an inviting option.
4. Hollow Brook Golf Club – Cortlandt Manor
Tucked a bit farther out, Hollow Brook brands itself as a “value club,” and it lives up to that label in the best way. It’s welcoming, scenic, and family-oriented. The clubhouse has that relaxed, rustic vibe, and the social side of the club is lively without being overwhelming.
Perfect for those new to the area—or new to the game.
5. Tamarack Country Club – Greenwich Border
Okay, this one’s technically in Connecticut, but it’s worth a mention for Bedford-area buyers who might find themselves right on the state line. Tamarack offers a refined experience with a family-first focus. The course is exceptional, the dining is top-tier, and there’s a spa for winding down after a frustrating round (not that I’d know anything about that).
It’s a splurge, sure—but a seriously beautiful one.
Thinking of Making the Move?
If you're considering a move to Bedford or anywhere nearby and wondering how the country club lifestyle fits in—let’s chat. I’m not here to pitch you on a membership or a house. Just sharing what I’m learning, what I’m loving, and what I hope to explore next.
Whether you're seeking public courses with great access, neighborhoods near clubs, or just someone to talk golf and Westchester life with—I’m around.
This is just five of many. What other courses do you love around Bedford, Westchester, or the Hudson Valley? Let me know—maybe we’ll meet out on the tee box.