Weekends work best, since several taprooms open late or close early on weekdays. Two weekends cover the whole trail. Hours also change from season to season, and small breweries come and go. Checking each brewery’s website before heading out saves a wasted trip, and every group needs someone sober at the wheel.

Day One: The North Shore, From Glen Cove to St. James

Much of this stretch follows Route 25A through the North Shore’s harbor towns.

Lunch on the Glen Cove Waterfront

Right by the water, Garvies Point Brewery & Restaurant occupies a renovated marina support building with a full kitchen.

• In docking season, boats up to 49 feet can tie up free while you eat.
• Inside, 100 seats face a bar overlooking the brewhouse, and 150 more spread outdoors.
• Juice Break IPA ranks among the house favorites on Untappd.

Mid-afternoon in Huntington

Next, the trail heads east into Huntington. On New York Avenue, Mark and Karen Heuwetter turned a 2,500-square-foot former dry cleaner into Six Harbors Brewing Company. The name honors the town’s six harbors, from Cold Spring to Northport. A fireplace warms the lounge in winter, and Bay Hill Blues, a blueberry wheat beer, joined the regular lineup after a popular seasonal debut.

Before Dinner in Northport

Along Main Street, Bill Kiernan and Kevin Sihler pour at Sand City Brewing Co. Their brand recalls a nearby mining site on Eaton’s Neck, which Steers Sand & Gravel renamed Sand City. Regulars tend to order Mofosaic, an IPA showcasing Mosaic hops.

Evening in St. James

Things wrap up on North Country Road at Saint James Brewery, which welcomes kids, dogs, and takeout from nearby restaurants. Off Fire Island, the Cunard liner S.S. Oregon sank in 1886. Generations later, diver and brewer Jamie Adams helped recover beer bottles from the wreck and revived the yeast they held. The brewery now ferments its Deep Ascent line with those strains.

Day Two: The South Shore, From Lindenhurst to Patchogue

The South Shore leg runs from Lindenhurst’s German roots to the edge of Patchogue Lake.

After Lunch in Lindenhurst

Lindenhurst once went by The City of Breslau, and Breslau Brewing Company now brews in that German tradition on a three-barrel system.

A short drive down Wellwood Avenue, a former 10,000-square-foot CVS became Sand City South, the Northport brewery’s second taproom. A 20-barrel brewhouse now sits where the pharmacy shelves once stood.

Toward Evening in Holbrook

Inland, 1940’s Brewing Company marks the year founder Charles Becker’s father graduated from brewing school. A long career in the trade followed. Today, a 10-barrel system turns out the taproom’s lineup, and Just Tap It In, a hazy New England brew, tops the brewery’s list on Untappd.

Dinner by Patchogue Lake

Two home brewers, Mark Burford and Pete Cotter, founded Blue Point Brewing Co. in 1998. Their West Main Street home housed Swezey’s department store, and later Briarcliffe College. Now, its kitchen turns out a full menu. Garage doors open toward Patchogue Lake, and Blue Point’s first brew kettle hangs above the bar as a chandelier. Toasted Lager, an amber lager, remains the signature beer.

Day Three: Manorville, Riverhead, and the North Fork

Riverhead sits where the two shores converge, and from there, Sound Avenue and Main Road lead past produce stands and vineyards.

Late Morning in Manorville

Just west of Riverhead, Long Island Farm Brewery works out of a former potato barn on the Waterdrinker Family Farm. Hops from the property go into Morning Dew, a wet-hop Kölsch. It’s a family- and dog-friendly stop, and parking belongs at Waterdrinker, not along the neighbors’ curbs.

Midday in Downtown Riverhead

Riverhead’s former fire department headquarters on East Second Street has housed North Fork Brewing Co. since 2018. Peter Barraud and Ian Van Bourgondien launched it together and grew their own hops in Peconic. Today, Barraud runs it as owner and head brewer. Past releases include Dark Side of the Maple, a porter, and Butternut the Hutt, a squash ale, and the taproom serves food.

Early Afternoon on Sound Avenue

Farther east, Jamesport Farm Brewery sits on land that once grew potatoes. It opened in 2017 as one of the North Fork’s earliest farm breweries, and a small hop field near the entrance grows Magnum, Columbus, and Centennial. The Windmill, a pilsner, ranks among the best sellers.

• Food trucks park on site daily, and the brewery doesn’t permit outside food.
• Most seating works on a walk-in basis, but groups of 10 to 25 can reserve an outdoor Hop Room.
• Limos, buses, and commercial vans need a reservation and must arrive before 2 p.m. The rule also covers drop-offs on or near the property.

Supper and a Nightcap Near Greenport

On Main Road in Peconic, Greenport Harbor Brewing Co. runs its larger location, with a restaurant, a beer garden, and an open field surrounded by North Fork vineyards.

In Greenport Village, the brewery got its start in an 1860s firehouse on Carpenter Street. Rich Vandenburgh and John Liegey, friends from Ohio Wesleyan University, renovated it to hold a brewhouse and a tasting room. Its walls double as a gallery for local artists. Established favorites include Harbor Ale, an American pale ale, and Black Duck Porter, though draft lists vary by location.

Day Four: Two Ferries to Sag Harbor

Across to Shelter Island

The final morning begins at the North Ferry dock in Greenport, where boats carry cars across to Shelter Island. Route 114 then leads to the South Ferry and a short crossing to North Haven. Right on Route 114 between the two docks, Shelter Island Craft Brewery posts daily summer hours. Its 114 IPA shares a number with the road.

The Last Stop in Sag Harbor

By afternoon, the trail ends at Kidd Squid Brewing Co., inside the village’s restored 1870 railroad freight depot on Spring Street. Each hazy IPA in its Moon Series celebrates a different full moon. Thanks to mostly New York ingredients, its farm brewery license lets it serve local wine, cider, and spirits as well. Early batches came from North Fork Brewing, the firehouse stop in Riverhead.

Trail’s End

Taken from start to finish, the trail traces the outline of Long Island. Two shores run side by side, meet in the middle, and give way to two forks reaching for open water. Each leg also works on its own for a single open Saturday.

Warm months favor the North Fork’s fields and vineyards and the ferry crossings. Colder afternoons suit fireside lounges and full kitchens closer to the city. However a group divides the route, the trail rewards an unhurried visit and good company.

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