The annual Westbury street fair draws a crowd on Post Avenue.

For nearly four centuries, the Village of Westbury, nearby Old Westbury, and the surrounding areas have perpetually flourished, nurtured by a central location on prime Long Island real estate. 

Earlier still, the stretch of Jericho Turnpike that winds through Westbury was once a trail used by Massapequa Indians. The view may be different today, but the commute is the same.

Back in the mid-1600s, when the first Europeans began settling the once-vast Long Island prairie known as the Hempstead Plains, an English Quaker named Edmond Titus built a homestead on a prime tract of grassland, amid 12,000 acres purchased purchased by Captain John Seaman in the 1640s from the Algonquian Tribe. Another Quaker settler, Henry Willis, christened the area “Westbury” in 1675, after his hometown of Westbury, Wiltshire, England. More Quaker families soon arrived, and by 1700 Westbury’s first Society of Friends meeting house was built.

Today, much has changed since Westbury’s humble Quaker beginnings. Westbury now boasts one of the most racially and culturally diverse populations on the Island, while Old Westbury — long a Gold Coast stomping ground — is regularly ranked one of the wealthiest places in America. That’s also why it’s a truly vibrant region to visit, whether you’ve got shopping, dining, or fun and games on your agenda.

The truth is, there are lots of reasons for visitors to spend time in Westbury, whether you’re from out of town, or just the next town over. Popular Westbury draws include:

NYCB Theatre at Westbury
NYCB Theater at Westbury

PASSION FOR THE ARTS

Long Island’s live entertainment scene owes a tremendous debt of gratitude to the NYCB Theater at Westbury (960 Brush Hollow Rd., 516-247-5200, thetheatreatwestbury.com), a.k.a. the Westbury Music Fair, consistently one of the area’s most enjoyable venues to catch a show at for generations. There’s really nothing quite like a performance on its ever-so-slowly rotating round stage, paired with the intimate feel of the room. What’s also great about the venue is the wide array of acts that come through; upcoming appearances include Los Lobos, Jay Leno, Styx, Dwight Yoakam, and John Cleese.

Westbury is also home to The Space at Westbury Theater (250 Post Ave., 516-283-5575, thespaceatwestbury.com), a vibrant and eclectic entertainment venue occupying the Tudor-styled former Westbury Movie Theater, first opened in 1927. Reborn in recent years, the Space is now an anchor of Post Avenue with its impressive façade, complemented by state-of-the-art lighting and sound systems within. Don’t miss upcoming performances by Carl Palmer, Phil Vassar and the ever-popular Pink Floyd tribute, the Machine.

An artist’s rendering of the exterior of Lesso Home in Westbury.

SHOP AND PLAY

Sometimes, a store is so popular, it ensures a steady stream of visitors to a neighborhood. That’s the case in Westbury with department store Century 21 (1085 Old Country Rd., 516-333-5200, c21stores.com), which beckons to fashion-savvy bargain hunters from all over the 516 and 631. The only thing more impressive than the selection are the prices.

Another of Westbury’s main shopping hubs, the Mall at the Source (1504 Old Country Rd., 516-228-2110), is in the process of being reborn as the mega home goods store Lesso Home New York Market. In the meantime though, some of the key remaining anchors of the old Source mall still provide ample reasons to visit; stop in and enjoy a meal at P.F. Chang’s or The Cheesecake Factory while you still can. It’s also a good excuse to hit the arcade at Dave & Buster’s, if you really need an excuse at all.

Better yet, find a few like-minded gamers and book a slot at Escape of a Lifetime (473 Old Country Rd., 516-780-4420, theescapeofalifetime.com), where you can choose from three different themed escape rooms, with varying levels of difficulty. Break into Da Vinci’s Study to steal his manuscripts, or pretend you’re a bank robber and flee The Vault before the cops arrive. Or, if you’re really up for a challenge, escape from The Asylum, before you become a permanent resident. 

THE LOUNGE OF LIFE

When the hustle and bustle of the Westbury area make you crave a little downtime, luckily there’s a long list of local watering holes and night spots where you can kick back and unwind in style. One neighborhood favorite is His & Hers Bar & Lounge (259 Post Ave., 516-385-3335), where the bartenders are friendly and you can order specialty martinis in flavors like mango, guava, tamarind, peach, and pineapple. Another popular hangout is Friar’s Tavern (231 Post Ave., 516-333-3893), located across from The Space, so it’s a slam-dunk choice for pre- or post-gaming a concert. You’ll also love the great drink prices and all-around good vibes.

For a vibe of an entirely different color, try The Polo Lounge (1100 Jericho Tpke., 516-333-7117, westburymanor.com/polo-lounge), a swanky, old-school restaurant and lounge with 1940s flair, located inside the Westbury Manor catering hall. There are no tables — just booths — perfect for relaxing and enjoying the top-flight food and expertly crafted cocktails. Similarly unique is the Mystique Hookah Lounge (973 Old Country Rd., 516-385-2320, mystiquehookahlounge.com), the area’s preferred location for sharing some shisha with friends. It’s open until 3 a.m. on Fridays and Saturdays, which is perfect for late-night smokers.

Old Westbury Gardens.

GOING GATSBY

Westbury’s fertile terrain wasn’t just prized in the past as farmland; in the 19th century it also attracted the New York elite, who came to hunt, ride, and play polo on the Hempstead Plains. This burgeoning new community of ultrawealthy landowners became the incorporated Village of Old Westbury in 1924, and today it’s still the home of one of the richest concentrations of Americans in the U.S. You may not be able to afford an Old Westbury address, but it sure is a nice place to visit.

There’s really no better (or cheaper) way to live like Old Westbury gentry than to spend a leisurely afternoon at Old Westbury Gardens (71 Old Westbury Rd., 516-333-0048, oldwestburygardens.org), the former estate of steel magnate John Shaffer Phipps. Converted to a museum in 1959, it is now open to the public for tours from late April through October. The centerpiece is Westbury House, built in 1906 by designer George A. Crawley, channeling 17th and 18th century English architecture. It is surrounded by 216 acres of landscaped formal and informal gardens, plus fields and woodlands. There’s no better reminder of why the area’s first settlers — up through its residents of today — are happy to call Westbury home.

WHERE TO STAY

Courtyard by Marriott Westbury Long Island
1800 Privado Rd., 516-542-1001, marriott.com

Hilton Garden Inn Westbury
1575 Privado Rd., 516-683-8200, hilton.com

Holiday Inn Westbury – Long Island
369 Old Country Rd., 516-997-5000, holidayinn.com

Red Roof PLUS+ Long Island – Garden City
699 Dibblee Dr., 516-794-2555, redroof.com

Viana Hotel & Spa
3998 Brush Hollow Rd., 516-338-7777, vianahotelandspa.com

WHERE TO DINE

Black Label Burgers
683 Old Country Rd., 516-333-6059, blacklabelburgersny.com

Café Baci
1636 Old Country Rd., 516-832-8888, cafebacirestaurant.com

Pollos El Paisa
989 Old Country Rd., 516-338-5858, polloselpaisali.com

Steve’s Piccola Bussola
649 Old Country Rd., 516-333-1335, stevespiccolabussola.com

Tesoro’s Ristorante
967 Old Country Rd., 516-334-0022, tesorosrestaurant.com

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Brendan Manley is an award-winning journalist, screenwriter and content development/marketing professional. He has extensive experience in newspaper and magazine publishing, as well as digital media, covering topics including arts and entertainment, sports, lifestyle, news, technology, travel and history. He is an ongoing contributor to Military History, Hotel News Now.com and HOTELS magazine, as well as the Long Island Press, where he formerly served as Managing Editor and Lifestyle section head. He is currently developing several of his original scripts for Hollywood, and consults on various film and scripted TV projects for studios, producers and financiers. Brendan is based in upstate New York's southern Adirondacks region.