Hudson Valley South · NY

Westchester

NY • Hudson Valley South

luxuryresortvaluepublic

Plan with AI

Best season

Summer-Fall

May · Jun · Sep · Oct

Trip cost · per golfer

$2,220–$4,800

4-night trip

Nearest airport

HPN

38 mi · HPN

Difficulty

mixed

Handicap 0–10

Overview

Why play Westchester

Discover Westchester for a golf experience blending historic championship courses with scenic Hudson Valley charm. Enjoy challenging layouts and impeccable conditions just a short drive from New York City.

Top courses

Best golf courses in Westchester

Editor-picked layouts ranked by prestige, conditioning and player experience.

Winged Foot Golf Club (West Course)

Design by A.W. Tillinghast · Par 72 · 7,477 yds

A classic A.W. Focus on accurate approach shots, as the greens are notoriously fast and undulating.

Extremely DifficultGolden Age, Tillinghast

Sleepy Hollow Country Club

Design by A.W. Tillinghast · Par 70 · 6,731 yds

A historic and picturesque Tillinghast design overlooking the Hudson River, offering stunning views and a challenging round. Take advantage of a caddie; their local knowledge is invaluable on this complex course.

DifficultGolden Age, Tillinghast

Pound Ridge Golf Club

Design by Pete Dye · Par 72 · 7,165 yds

Pete Dye's only design in New York, featuring dramatic elevation changes, rock formations, and challenging bunkers. Bring extra balls, as the course is visually stunning but unforgiving for errant shots.

Very DifficultModern, Target Golf$200–300

Rye Golf Club

Design by Donald Ross · Par 71 · 6,431 yds

A classic Donald Ross design offering a public golfing experience with views of Long Island Sound and challenging greens. Walk the course if you can; it's a great way to appreciate the classic Ross contours.

MediumGolden Age, Ross$100–150

Stay & play

Where to stay in Westchester

Resort packages bundle lodging, rounds, range access, and on-site dining. Hotel-only options give you flexibility to course-hop.

The Ritz-Carlton New York, Westchester

Luxury Hotel

A luxurious hotel in downtown White Plains offering upscale amenities and impeccable service.

Hyatt House White Plains

Mid-range Hotel

Modern and comfortable extended-stay hotel with spacious suites, ideal for longer golf trips.

Cambria Hotel White Plains Downtown

Boutique Hotel

Stylish hotel with contemporary design and convenient access to local attractions and dining.

Courtyard by Marriott Rye

Standard Hotel

Reliable and comfortable hotel near Rye Golf Club, offering a pleasant stay for golfers.

Off the course

Things to do in Westchester

Non-golf experiences worth building into your trip — from local landmarks to nature, food, and culture.

Kykuit, The Rockefeller Estate

Historical Tour

Tour the historic home, gardens, and art collections of the Rockefeller family in Pocantico Hills.

Walkway Over the Hudson State Historic Park

Outdoor Recreation

Stroll or bike across the world's longest elevated pedestrian bridge, offering stunning views of the Hudson River.

Stone Barns Center for Food & Agriculture

Educational/Food

Explore a working farm and educational center focused on sustainable agriculture and culinary innovation.

Philipsburg Manor

Historical Tour

Step back in time at this living history museum depicting colonial life in the Hudson Valley.

Shopping at The Westchester

Shopping

Indulge in upscale retail therapy at this premier shopping mall in White Plains, featuring luxury brands.

Itineraries

Sample itineraries

Choose your trip length. Each plan is built around the marquee courses, with rest, dining, and travel days dialed in.

1
Day 1
Arrive & warm up
Land at HPN, transfer to your hotel, hit the range, and grab a casual dinner at Iron Horse Grill.
2
Day 2
Round 1 — Winged Foot Golf Club (West Course)
Morning tee time at Winged Foot Golf Club (West Course). Lunch at the clubhouse, afternoon recovery, dinner at Oceanique.
3
Day 3
Final round & departure
Early tee time at Rye Golf Club, light lunch, then transfer back to HPN.

Budget

Budget breakdown · per golfer

Realistic ranges sourced from current resort rates, public green fees, and group dining averages.

Lodging 4 nights · $317/nt	$1,268
Golf 3 rounds · $185 avg	$555
Food & drink ~$110/day	$440
Ground transport Rideshare + cart fees	$240
Flights Search Skyscanner for live fares	Variable
Estimated total · per golfer	$2,503

Season

Best time of year to visit Westchester

humid continental

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Ideal Good Off-season

When to book: 3-6 months out

Dining

Where to eat in Westchester

From clubhouse classics to chef-driven dinners worth a reservation.

Iron Horse Grill

American

A popular spot in Pleasantville with a vibrant atmosphere and delicious, inventive American fare.

Goosefeather

$$$

Modern Cantonese

Chef Dale Talde's acclaimed restaurant in Tarrytown, offering exceptional Cantonese food with a modern twist.

Oceanique

$$$

Seafood

An upscale seafood restaurant in White Plains known for its fresh catches and elegant ambiance.

Walter's Hot Dogs

American (Hot Dogs)

An iconic roadside stand in Mamaroneck serving delicious, crispy, split hot dogs since 1919.

Crabtree's Kittle House Restaurant & Inn

$$$$

Farm-to-Table American

A historic inn and restaurant in Chappaqua offering exquisite farm-to-table dining and an extensive wine list.

Terra Rustica

Italian

A charming authentic Italian restaurant in Yorktown Heights, known for its homemade pasta and cozy atmosphere.

After dark

Nightlife in Westchester

Where the buddy trips end up after the 19th hole.

White Plains Beer Hall

Beer Garden

A lively beer garden offering a wide selection of craft beers, pub food, and a relaxed atmosphere.

The Brazen Fox

Pub/Bar

A popular gastropub in White Plains known for its extensive whiskey selection, craft beers, and live music nights.

Morton's The Steakhouse (Bar Area)

Cocktail Bar

An upscale bar in White Plains, perfect for pre or post-dinner drinks with a sophisticated ambiance.

Tee times

Book tee times in Westchester

Live inventory from GolfNow plus flight comparison from Skyscanner. Prices update in real time.

FAQ

Westchester golf trip FAQs

What is the best time of year to golf in Westchester?

Summer-Fall (May, Jun, Sep, Oct). humid continental

How much does a golf trip to Westchester cost?

Plan on $2,220–$4,800 per golfer for a 4-night trip including lodging, rounds, food and ground transport. Flights are extra.

What airport should I fly into for Westchester?

HPN, about 38 miles from the resort area. Most national hubs offer non-stop service via HPN.

How many days should I plan for a Westchester golf trip?

4 nights is the sweet spot — enough for 3 full rounds plus a rest or sightseeing day.

Is Westchester good for buddy trips?

Yes — popular with corporate, solo. Quieter evenings, ideal for golf-focused groups.

Ready to book

Book your Westchester golf trip

Lock in tee times on GolfNow, secure your stay on Booking.com, or let our AI planner build the entire itinerary for your group in under a minute.

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Trip snapshot

Destination

Westchester, NY

Best months

May, Jun, Sep, Oct

Length

4 nights

Per golfer