Sayville takes the holidays seriously, with winter festivals, parades and carolers.

Like many of its neighboring South Shore communities, Sayville has always had an indelible connection with the water, and its prime location on the Great South Bay continues to inspire both visitors and residents to converge upon the venerable Long Island hamlet. Once prized for timber and oysters, today Sayville delights with quaint downtown charm, fabulous dining and a host of historic, outdoor and recreational pursuits.

Although settled in 1761 by John Edwards, Sayville — once known as simply “over south” — didn’t earn a proper name until 1838, after its first post office had opened the year prior. As the story goes, one resident had suggested the name “Seaville,” but the moniker later became “Sayville,” when the town clerk referred to an old Bible, which spelled the word “sea” as “say.” Thus “Sayville” was the spelling the clerk sent to Washington, D.C., for registration, and although the community later protested, the name stuck. The alternative spelling hasn’t seemed to hinder Sayville’s prosperity over the ensuing centuries.

“Like many hamlets in the Town of Islip, Sayville is a lovely community,”  says Islip Town Supervisor Angie Carpenter. “It offers a sense of place for families, young professionals and many seniors. Shopping and dining experiences from casual to fine dining, as well as gift shops and specialty boutiques, are available within walking distance. Our pleasant community parks and Town beaches are easily accessible, and a short ferry ride brings passengers to the world-class, white-sand ocean beaches of Fire Island.” 

Like nearby Patchogue, Sayville is widely known as a key hub for ferries to Fire Island, just across the bay. In a tradition dating to 1894, the Sayville Ferry Service (41 River Rd., 631-589-0810, sayvilleferry.com) makes regular trips to the Fire Island communities of Cherry Grove, Sailors Haven, Fire Island Pines and Water Island. Check the website for the latest departure and arrival schedules.

But if you’re not headed over to the barrier beach, fret not: Sayville has a lot more to offer than just its ferry terminal. Don’t miss some of these essential Sayville hot spots.

CELEBRATING THE PAST

Start your journey by soaking up Sayville’s rich seafaring history, at the Long Island Maritime Museum (88 West Ave., West Sayville, 631-854-4974, limaritime.org), set on 14 beautiful waterfront acres from the former Meadowedge estate, once the home of Mr. and Mrs. Anson Wales Hard. It features a large collection of small vessels built or used around Long Island, including multiple sailboats constructed in Patchogue by iconic LI shipbuilder Gil Smith. There’s also an interactive lifesaving exhibit, a circa-1908 oyster house, an 1890 bayman’s cottage and the 1888 Oyster Sloop Priscilla, a National Historic Landmark. For the kids, the museum also offers winter and spring break programs, as well as summer camps.

Then, immerse yourself in 19th century South Shore architecture at Islip Grange Park (10 Broadway Ave., 631-472-7016, sayville.com/parks.asp#grange), boasting a collected “village” of restored authentic early buildings that have been moved to the 12-acre park from their original locations. Structures like the Bicentennial Cottage, Dutch Reformed Church, Estate Managers Cottage, Ockers Barn and The Mill provide a striking portrait of the lifestyle and aesthetics in a pre-Civil War Long Island hamlet.

History buffs can also experience Sayville’s early 20th century Gold Coast era at the Meadow Croft estate (299 Middle Rd., 631-472-4625, bayportheritage.org/meadowcroft.asp), formerly the summer home of John E. Roosevelt and family. Now owned by Suffolk County, Meadow Croft is composed of a restored 19th century farmhouse (including an 1891 addition designed by Sayville’s Isaac H. Green Jr.) as well as a carriage house, an auto house, a caretaker’s cottage and a swimming pool. The main house features some impressive original Roosevelt family items, including a grand piano and the original dining room set, where in 1903 the family hosted a lunch with former President Theodore Roosevelt, who was John’s cousin.

Downtown Sayville is a Long Island shopping mecca.

ON THE BALL

As integral as Sayville’s historical attractions may be, no seaside vacation (or daylong excursion) is complete without a little mini golf, as well. In Sayville, the putting frenzy goes down at Sayville Falls Mini Golf (30 Hanson Pl., 631-256-5632, sayvillefallsminigolf.com), which is known for its attractive, well-manicured course. There are numerous water features, including waterfalls, streams and pools, so putt with caution, or prepare to go fishing for your ball. The course is also a popular destination for special events, parties, and camp group visits.

Sayville’s spherical fun doesn’t stop there, either. Bowlers regularly flock to Bowlero Sayville (5660 Sunrise Hwy., 631-567-8900, bowlero.com) to get their fix; the recently revamped 50,000-square-foot bowling alley now features 60 lanes of black-light bowling, plush lane-side lounge seats, high-definition video walls and an extensive snack bar menu. There’s also a retro-themed cocktail lounge, video arcade and popular party games, like cornhole and beer pong. If you spend more time racking up gutter balls than rolling strikes, you can always blame the booze.

A dramatic sunset at a Sayville marina. (Shutterstock)

WIDE OPEN SPACES

Be sure, though, not to spend your entire trip to Sayville just bowling and playing beer pong. Get outside and enjoy nature too, especially at Sans Souci County Park (Broadway Ave., 631-854-4949, suffolkcountyny.gov), named for the French phrase “without worry.” Living up to its billing, a stroll through this 316-acre nature preserve — once a cranberry farm — will literally make your worries melt away. Three different nature trails originate at the preserve’s parking lot.

Another favorite Sayville spot for a stroll is The Common Ground at Rotary Park (located between Gillette and Candee Aves., 631-459-6603, thecommonground.com), a reflective garden created by community members in memory of the victims of the Sept. 11, 2001 terrorist attacks. The Common Ground features lush gardens, walkways lined with personalized stones, memorial benches, the Peace Labyrinth and the Pamela Raymond Performance Pavilion, where outdoor concerts are regularly held (often as part of the Wednesdays in the Park weekly event). Other special events there include Family Fridays, Yoga in the Park, and special labyrinth walks.

And if the salt air is what you crave, head over to the Sayville Marina Park (400 Foster Ave., 631-854-4949, sayville.com/parks.asp#marina), offering a lengthy pier where you can relax on benches, do some fishing in the bay and enjoy classic Long Island waterfront scenery. The park — former site of the massive Tidewater Inn, which was built in 1916; the inn became known as the Shoreham in 1937 and burned down in 1973 — also includes a playground, picnic tables, tennis courts, boat docks and a small beach.

DRINKING AND DIPPING

Perhaps the most surprising Sayville attraction is Loughlin Vineyard (253 S Main St., 631-589-0027, loughlinvineyardny.com), which saves many wine lovers from having to make a trip to the East End, where the majority of LI’s vineyards historically reside. A family business for the last 34 years, the vineyard is located on the grounds of John E. Roosevelt’s former Meadow Croft estate, where it typically produces five wines per year from its 7-acre crop. Spend an afternoon tasting Loughlin’s popular red, white, and blush wines, then enjoy a picnic lunch (bring your own) among the grapes.

After you’ve purchased that perfect bottle of wine (or 10) at Loughlin, head over to the Crushed Olive (31A Main St., 631-256-5777, thecrushedolive.com), which is part of a local chain of stores that now have six LI locations. Sample the selection of extra virgin and infused olive oils, aged balsamic vinegars, and various other gourmet oils, then watch them fresh-bottle and cork your selection(s). Recommended varieties to try include the espresso balsamic and dark chocolate balsamic vinegars, which pair well with ice cream or fresh fruit, as well as the lemon-infused olive oil. Online shopping is available on the Crushed Olive website, in case you run out before your next Sayville visit.

There is no shortage of shops in downtown Sayville.

WHERE TO DINE

Butera’s
100 S. Main St., 631-563-0805, buteras.com/sayville

Bistro 25
45 Foster Ave., 631-589-7775, bistro25li.com

Off The Block
501 Montauk Hwy., 631-573-6655, offtheblockmeats.com

Café Joelle on Main Street
25 Main St., 631-589-4600, cafejoelle.com

Cull House
75 Terry St., 631-563-1546, cullhouse.com

Cricket’s
98 Main St., 631-567-6345, cricketssayville.com

Aegean Café
35 Main St., 631-589-5529, sayvilleaegeancafe.com

Downtown Burger at Five Points Café
1 Main St., 631-567-5655, fivepointscafe.com

WHERE TO STAY

Land’s End Motel & Marina
70 Browns River Rd., 631-589-2040, motel.landsendweddings.com

Sayville Motor Lodge
5494 Sunrise Hwy., 631-589-7000

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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.