Dickensian characters such as Father Christmas roam the streets of Port Jefferson during the village’s annual Charles Dickens Festival. (Photo by Ron Ondrovic)

The Port Jefferson we know today is a thriving hub for tourism on Long Island’s North Shore, drawing countless ferry-goers, shoppers, diners and bar patrons to the village’s brimming enclave. For many Long Islanders it is the go-to spot for a romantic date, and few simple pleasures can match spending a sunny day enjoying an ice cream cone and a walk down its colorful streets.

Port Jefferson has changed dramatically over the last two centuries, transforming from a rural community in the 1700s to a vibrant shipbuilding town in the 1800s, to the nightlife and leisure destination of modern times. The village’s ferry line to Connecticut, as well as its Long Island Rail Road station, ensure a steady stream of visitors year-round.

“When they come for the day, they can actually stay for the weekend,” Port Jefferson Village Mayor Margot Garant says while inviting visitors to try the dining, entertainment and hotel options.

Each December, tourists descend upon the village for the annual Port Jefferson Village Dickens Festival, complete with revelers dressed in 19th-century clothing, house tours, winter-related poetry readings, caroling and booths featuring local businesses. The village also hosts an annual outdoor concert series and film screenings at Harborfront Park throughout July and August. And of course, its its own annual boat race series — the Village Cup Regatta — with proceeds benefiting cancer research.

But that’s just the beginning of the village’s many charms. Other perennial Port Jefferson draws include:

The Port Jeff ferry shuttles travelers across the Long Island Sound to and from Bridgeport, Conn.

The Back and Forth

Port Jefferson is a bustling Long Island ferry port, which means there’s a constant flow of passengers departing and arriving, especially during summer months. For a quick and easy trip across the Long Island Sound to Connecticut (and vice versa), the Bridgeport & Port Jefferson Steamboat Company (102 West Broadway, 888-443-3779, 88844ferry.com) has multiple trips available per day. Arrive early and grab a bite at one of the neighboring eateries while you wait.

Arts & Culture

Port Jefferson is the kind of venerable waterfront community that screams maritime history, and an informative and engaging overview of that heritage — primarily geared toward kids — can be found at the Maritime Explorium (101 East Broadway, 631-331-3277, maritimeexplorium.org) overlooking the harbor. It offers hands-on exhibits devoted to the historical, scientific and artistic aspects of the area’s seagoing past and the Long Island Sound’s unique ecosystem, where children can learn at their own pace through playful experimentation. There are also several exhibits devoted to emerging nanotechnologies and their application to oceangoing life and industry.

You can also step back in time at the Mather House Museum (115 Prospect St., 631-473-2665, portjeffhistorical.org/the-matherhouse), the former home of the Mather family, circa 1840 to 1860, who were prominent shipbuilders in the area. The museum complex includes the Mather House, featuring period furnishings, fine and decorative art, model ship hulls and an early kitchen, as well as the Craft House & Museum Shop, the Country Store, the Marine Barn and Sail Loft, the Tool Shed and the Thomas Jefferson Perennial Garden. The museum is open Wednesday to Sunday, from noon to 4 p.m., from May 27 to Oct. 8. A docent guided tour is available for the main museum and complex buildings.

For theatergoers, local theater is alive local theater is alive and well in Port Jefferson at Theatre Three (412 Main St., 631-928-9100, theatrethree.com), which presents a wide range of performances through its Mainstage, Second Stage, Cabaret and Children’s Theatre productions. It also hosts Friday Night Faceoff, Long Island’s longest-running improv troupe, as well as its Dramatic Academy, offering three instructional semesters each year, plus a diverse summer concert series. Upcoming performances include A Christmas Carol, I Hate Hamlet and 12 Angry Men on the Mainstage, and Barnaby Saves Christmas, Rapunzel: The Untold Story! and The Adventures of Peter Rabbit in the Children’s Theatre.

Hundreds of performances annually grace the stage of Theatre Three in the historic Athena Hall.

Drink Me

Strolling through the village can make you work up a terrific thirst, but luckily Port Jefferson offers several renowned watering holes where you can duck in for a frosty pint and maybe even some grub, if the mood hits you. Start with the Port Jeff Brewing Company (22 Mill Creek Rd., 877-475-2739, portjeffbrewing.com), which uses a seven-barrel system to produce 217 gallons (about 86 cases) of remarkable beer per brew. The tasting room is open all year, serving up tasting flights, pints and beer to go, poured from 11 taps that change daily (check the website for the day’s selections). The brewery also hosts a free summer concert series every Wednesday night June through August.

You also can’t go wrong at the Tara Inn (1519 Main St., 631-828-5987) a bona fide Port Jeff classic adored for its friendly atmosphere, reasonable prices and massive food portions. In a world of increasingly foofoo fanciness, bask in Tara’s simple oldschool charm while ordering from its menu, displayed on chalkboards and paper plates hung on the wall. There’s no takeout offered, no substitutions or special orders allowed, and no credit cards accepted. Deal with it.

If you prefer vino to suds, you don’t need to trek all the way out to the East End for winetasting, thanks to the Pindar Vineyards Port Jefferson Wine Store (117 Main St., 631-331-7070, pindar.net), featuring a range of the winery’s incredibly popular varietals and seasonal wines. For just $10 you can sample five different wines, or if you’d like a souvenir, too, toss in an extra buck ($11 total) and you can keep the glass. The shop also sells wines produced by its sister winery Duck Walk Vineyards, although those labels aren’t available for tasting. Be sure to check out the special seasonal mulled wine, which is only offered during the winter.

No trip to Port Jeff is complete without a meal at The Steam Room.

Brain Teasers

The proliferation of “escape rooms” throughout the region has reached the shores of Port Jeff, too, where there are two options for cramped, mind-melting fun: Hour Escape (1303 Main St., 631-403-3030, hourescapeportjeff.com) and Know Escape (1518 Main St., 631-241-1239, knowescapeportjefferson.com). Hour Escape offers two different escape scenarios: Café Lorenzo, a mafia-themed challenge set in an Italian restaurant; and Exit Protocol, a hacker-themed setting in which you must locate classified documents in a top-secret government facility. Know Escape, meanwhile, takes a somewhat different approach, with one mystery spread throughout three rooms that teams must navigate. The current scenario there is called Sunderland Hollow, and focuses on the bizarre, chilling events in a mysterious town.

Harborfront Park is the hub of entertainment in downtown Port Jeff.

Shopper’s Haven

High-end olive oil shops have become a burgeoning trend on Long Island and elsewhere, and Port Jeff hasn’t been left out of the bread-dipping frenzy. The Amazing Olive (213 Main St., 631-509-4596, amazingolive.com), which also has a shop in Patchogue, is celebrating its five-year anniversary in Port Jeff, and from the looks of things, there are many more years of gourmet goodness ahead. The shop carries the finest extra virgin olive oils, vinegars, herbs, salts, rubs and seasonings in the area, perfect for luxurious gifts or your own day-to-day pantry. Stop in and sample more than 50 award-winning oils before making a decision. The shop also holds private tasting parties Monday through Thursday after closing, complete with appetizers, a balsamic-inspired drink and dessert for each guest ($20 per person, six to 14 adults). After the tasting you get the entire store to yourself to browse and buy, plus a free sample bottle of oil to take home.

And that’s just the beginning. There’s a bounty of fine shops in the village that literally offer something for everyone. If art is your forte, there’s the Thomas Kinkade Signature Gallery (128 Main St., 631-642-0607, thomaskinkadehq.com), displaying and selling a compendium of the artist’s works, including his popular creations for Disney and DC Comics. Or, explore spirituality, metaphysics and New Age dogma at Breathe (116 E. Main St., 631-642-2377, breatheinspiringgifts.com), the local mecca for everything from crystals to essential oils to tarot cards. The shop also offers psychic and medium readings, guided meditation and a range of classes and workshops.

Danfords Hotel in Port Jefferson also operates a spa and marina in the heart of the village.

The Great Outdoors

While visiting Port Jefferson, don’t forget to enjoy the scenic beauty of the area. A favorite spot for stunning views and photo ops is McAllister County Park (200 Cliff
Road), a Suffolk County park that runs along the beach, sometimes called “Pirates’ Cove” by locals. The only downside to this hidden gem is the limited parking, but if you’re lucky enough to find an open spot, the park offers an oasis of waterfront tranquility, perfect for a romantic walk or contemplative stroll. Amid all the fun and food in Port Jeff, you’ve also got to take a moment or two to let the simple joys soak in.

Where To Stay In Port Jefferson

Danford’s Hotel, Marina & Spa
25 E. Broadway, 631-928-5200, danfords.com

The Fox and Owl Inn
1037 Main St., 631-509-3669, thefoxandowlinn.com

The Ransome Inn B&B
409 E. Broadway, 631-474-5019, ransomeinn.com

Holly Berry Bed and Breakfast
23 Dickerson Ct., 631-331-3123

Golden Pineapple Bed and Breakfast
201 Liberty Ave., 631-331-0706, goldenpineapplebandb.com

Where To Dine In Port Jefferson

Toast Coffeehouse
242 E. Main St., 631-331-6860, toastcoffeehouse.com

The Fifth Season
34 E. Broadway, 631-477-8500, thefifth-season.com

Pasta Pasta
234 E. Main St., 631-331-5335, pastapasta.net

Slurp Ramen
109 W. Broadway, 631-509-1166, slurpusa.com

The Steam Room
4 E. Broadway, 631-928-6690, steamroomrestaurant.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.