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The view of Jamesport from above. (Credit: David Benthal)

There’s a turning point as you head east into Aquebogue and Jamesport. 

The big box stores that dot Route 58 in Riverhead suddenly feel hundreds of miles away — not five as the GPS reminds — as you enter Aquebogue and Jamesport. 

The first communities flanked by both the Peconic Bay and the Long Island Sound, it’s where the small town coastal ambience that radiates across the North Fork begins. 

As Route 58 fades into Route 25 at the start of Aquebogue heading into Jamesport the shift is subtle, but instantaneous. The two-lane highway turns into one and scenes of farm fields and vineyards come into view.

There are several farm stands and markets for fresh produce and local provisions on your journey — Bay View Farm Market among the most prominent on the main drag.

The downtown Main Street is deceptively small in comparison to all its offerings. 

Dinning satisfies every craving. The newly opened Main Road Biscuit Co. has become a popular breakfast and lunch spot  — get those chicken and waffles — while Junda’s Pastry Crust & Crumbs across the street never fails to deliver with its locally famed strudel. 

A traditional steak dinner calls for the tried-and-true Cliff’s Elbow Room, while crave-worthy tacos are found just west of downtown at the recently opened Little Lucharitos.

Jamesport has two notable restaurants for fine dining the Jedediah Hawkins Inn and Jamesport Manor Inn. Each boast farm-to-table menus and the former also features storied accommodations in close proximity to Main Street. Bay Breeze Inn & Bistro — slightly off the beaten path in South Jamesport — offers a lodging option for those who prefer to be steps away from the beach and a park for picnicking. 

The juxtaposition between old and new in Jamesport is hard to deny. The centuries old Jamesport Meeting House anchors the downtown and still serves as a place for community gatherings. Just around the corner at the Red Salvage Barn, antique furniture and wood reclaimed from historic North Fork barns and houses gets new life with on-trend painting techniques and treatments. 

If it’s imbibing you seek, you’ll find it here. 

Names and numbers

English name: Jamesport

Indian name: Aquebogue/Occabauk

Settled: 1690s

Area: 4.5 square miles

Population: 1,710

ZIP code: 11947

School nickname: Blue Waves

There are a handful of award-winning wineries throughout the hamlet. Jamesport Vineyard is the place for local wine in a relaxed outdoor setting while Sherwood House has a cozy fireplace that warms souls on brisk spring evenings. Paumanok Vineyards in Aquebogue is renowned for its stellar winemaking reputation.

Martha Clara and Palmer Vineyards are popular stops on the north side of the hamlet, where you’ll also find Jamesport Farm Brewery. The Sound Avenue brewery is a haven for craft beer enthusiasts looking to sip the terroir from something other than a wine glass. 

Located on the Long Island Sound, the recently established Hallock State Park Preserve across the street from Martha Clara is the premiere place to catch a sunset and enjoy a hike. A visit to the hamlet would be remiss without a stop at Hallock Museum Farm next to the preserve. The historic campus is a testament to Riverhead Town’s potato farming roots and home to particularly adorable farm animals. 

Jamesport is a hamlet of new and old — quintessentially North Fork in every way.