The Smithtown Bull statue greets visitors on Route 25. (Long Island Press photo)

You can’t miss it as you drive through the hectic intersection of Routes 25 and 25A in Smithtown: a massive statue of a bronze bull, the type which looks more at home on Wall Street than a busy Long Island thoroughfare. And as you might imagine of any farm animal deemed worthy of a statue, in Smithtown — first settled around 1665 — the monument honors no ordinary bull. 

According to the popular—albeit largely fictional—story, English settler Richard Smythe rescued the captured daughter of a Native American chief, who rewarded Smythe by granting him all the land Smythe could encircle in one day on a bull. (Historians say it was really Lion Gardiner, not Smythe, who rescued the daughter. Chief Wyandanch then gave Gardiner the land, which Smythe either bought or won in a card game.)

The myth, however, has a more memorable conclusion: Smythe, apparently no dim bulb, purportedly opted to ride “Whisper,” his prized bull, on the summer solstice — the longest day of the year — thereby acquiring the land once called “Smithfield,” and now known as Smithtown. The bull, meanwhile, got a statue.

Now 350 years later, Smithtown remains as vital a component of the North Shore tapestry as ever. Today, it comprises one of Long Island’s most active and colorful townships, offering fine dining, eclectic retail, historic and natural attractions, arts and entertainment, nightlife and a host of outdoor recreational options. It’s a great place to work, live and visit, and continues to evolve and expand with the times.

Of course, no trip to Smithtown is complete without a quick gander at the bronze Whisper the Bull Statue at the crossroads of Routes 25 and 25A. And by quick, I mean you’ll literally need to look quickly as you drive past, since there’s nowhere nearby to park. Instead, tap your horn in reverence of the majestic creature as you whizz by. After that, our other mandatory Smithtown suggestions include:

Other photo goes on page 2: A crisp blue sky filled with fluffy clouds over the mouth of the Nissequoque River of Long Island. (Getty Images)

GREEN LIVING

Smithtown strikes a healthy balance between picturesque natural scenery and modern suburban convenience. To bask in the former, there’s Caleb Smith State Park Preserve (581 West Jericho Tpke., 631-265-1054, parks.ny.gov/parks/124), boasting 543 passive-use acres and multiple habitats, accessible by several hiking trails. Keep an eye out for birds like prothonotary warblers, Virginia rails and osprey, as well as rare plants like pink lady slipper, trailing arbutus and Indian pipe. There’s also its recently renovated Nature Museum, which presents nature programs and natural history exhibits, including a great blue heron, red fox, flying squirrel and river otter. Fishing is permitted, in season, on the Nissequogue River and Willow Pond; in winter, trails double as paths for snowshoeing and cross-country skiing.

If your hike at Caleb Smith doesn’t yield enough wildlife sightings (or if you just dig animals), continue on to Sweetbriar Nature Center (62 Eckerncamp Dr., 631-979-6344, sweetbriarnc.org), a haven for natural science education and wildlife rehabilitation. Located on 54 acres of gardens, woodlands, fields and wetlands on the Nissequogue, hundreds of species of plants and animals reside there. Stroll through the outdoor enclosed Butterfly Vivarium; meet the denizens of the Reptile Room and Rainforest Room; play in the Discovery Area; and create in the Art Center. Many special events are also held at Sweetbriar throughout the year, as well as children’s environmental education weeks and birthday parties.

And it would be downright criminal to not specifically mention the many advantages of Smithtown’s prime location on the Nissequogue River. When weather permits, a day spent paddling this scenic waterway is the very definition of idyllic, and Nissequogue River Canoe & Kayak Rentals (Paul T. Given County Park, Routes 25 and 25A, 631-979-8244, canoerentals.com) is there to make it happen for you. Trips begin (or end) at the Nissequogue River State Park in Kings Park, or the headwaters at Smithtown’s Paul T. Given County Park. Transportation to and from the launch is provided.

The Smithtown Center for the Performing Arts is in the heart of downtown Smithtown..

UNDER THE LIGHTS

Smithtown’s convenient, central location on Suffolk’s North Shore makes it an ideal destination for arts and cultural events, notably at the Smithtown Center for the Performing Arts (2 E. Main St., 631-724-3700, smithtownpac.org), presenting a range of musical and theatrical events throughout the year. Now entering its 18th season, the center’s 2019-20 calendar includes performances of Annie, The Taming of the Shrew, Green Day’s American Idiot: The Musical, The Addams Family, and A Chorus Line. There’s also a children’s theatre and upcoming special appearances like The Cast of Beatlemania (multiple dates) and Desert Highway Band’s tribute to the Eagles (Dec. 14).

POTENT POTABLES

Wine tasting on Long Island is always a surefire activity, but you might not always have the time for a lengthy ride out to the East End. That’s why it’s all the more enticing that Smithtown is home to Harmony Vineyards (169 Harbor Rd., Head of the Harbor, 631-291-9900, harmonyvineyards.com), sustainably farmed by viticulturist Stephen Mudd and featuring wines crafted by Eric Fry. Sample Harmony’s Bordeaux-style red blends, Chablis-style chardonnays, local beers and gourmet plates year-round in its historic circa-1690 waterfront tasting room and vineyard terrace. Special events include “Drink-In Theatre” on Friday nights and “Tasting Notes Jazz Club” on Thursday and Saturday nights.

Smithtown’s drinking and nightlife scene isn’t all fancy wines and exotic cheeses, either. There are several time-honored watering holes in town where the drafts flow, the wings sizzle and the big-screen TVs glimmer. Croxley Ale House Smithtown (155 W. Main St., 631-656-8787, croxley.com) is one can’t-miss choice, with 52 varieties of beer and cider on tap, 34 bottled brands and six more served in cans. Check out the new and seasonal varieties, the extensive dining menu and the weekly specials, including Taco Tuesdays, Wednesday Historic Wing Nights and Happy Hour specials Monday through Friday.

Similarly classic and heavily frequented is Napper Tandy’s Irish Pub (15 E. Main St., 631-360-0606, nappertandysirishpub.com), which hosts a steady calendar of live bands and a young, lively crowd of partyers. Weekly drink specials and themed nights keep the beverages flowing, as well as Napper’s All-Day Happy Hour from Monday through Friday. There’s also a surprisingly intriguing dining menu, with atypical pub grub like duck empanadas with Thai chili sauce and Brussels sprouts with honey lime Sriracha sauce, alongside classic burgers, fish and chips and shepherd’s pie.

A night out in Smithtown can even take on an otherworldly twist. One of the town’s most mythical hangouts, Katie’s of Smithtown (145 W. Main St., 631-360-8556, katiesofsmithtown.com), regularly packs ‘em in thanks to its friendly bartenders, back patio and live music, but the establishment is also reportedly haunted, so there’s that, too. And while I can’t guarantee you’ll experience the supernatural yourself, you’ll definitely want to haunt Katie’s brand-new food truck. Even more legendary than the purported ghosts is Katie’s signature mac daddy cone: a waffle cone stuffed with creamy mac and cheese. Nothing scary there.

Maureen's Kitchen
Maureen’s Kitchen co-owners Christine Fortier and her brother, Kevin Dernbach. Their sister, Doreen Migliore, is also on staff. (Rashed Mian/Long Island Press)

WHERE TO DINE

Aji 53
1 Miller Pl., 631-979-0697, aji53.com

Café Havana
944 W. Jericho Tpke., 631-670-6277, cafehavanali.com

Casa Rustica Restaurant
175 W. Main St., 631-265-9265, casarustica.net

Chop Shop
47 E. Main St., 631-360-3383, chopshopbarandgrill.com

Ciro’s Pizza
546 Smithtown Bypass, 631-724-5745, cirospizzany.com

The Garden Grill
64 N. Country Rd., 631-265-8771, thegardengrill.com

H20 Seafood & Sushi
215 W. Main St., 631-361-6464, h2oseafoodsushi.com

Javier’s Cafe
101 E. Main St., 631-406-7712, javierscafe.net

Maureen’s Kitchen
108 Terry Rd., 631-360-9227

Thai House
53 W. Main St., 631-979-5242, thaihousesmithtown.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.