Route Description
NY 27A begins at a large junction between NY 27 (the Sunrise Highway) in front of Westfield Sunrise Mall in the town of Oyster Bay, just east of Massapequa. NY 27A proceeds east along Old Sunrise Highway for one block, turning south on Carman Mill Road, which consists of several blocks of residential homes and passing a local school. Several blocks to the south, NY 27A intersects with Merrick Road at a t-intersection. At Merrick Road, NY 27A turns east off Carman Mill and onto Merrick, a four-lane boulevard through the town of Oyster Bay and the hamlet of East Massapequa. NY 27A is commercial for a long distance across East Massapequa, soon bending northeast into an intersection with County Route 1 (County Line Road).
At the intersection with CR 1, NY 27A and Merrick Road cross into Suffolk County and the town of Amityville. Now just a two-lane arterial through Amityville, NY 27A crosses east through a commercial section, intersecting with the southern terminus of NY 110 (Broadway) and bending southeast at an intersection with Richmond Avenue. Crossing over a small waterway that drains into the Great South Bay, the route passes south of Amityville Memorial High School. After crossing another waterway, NY 27A crosses into the town of Babylon. Now in the Copiague section of Babylon, the route proceeds northeast through Copiague, intersecting with the southern end of CR 47 (Great Neck Road). Once again a four-lane boulevard, NY 27A crosses into the village of Lindenhurst, now boasting the West Montauk Highway moniker.
NY 27A through Lindenhurst remains commercial, passing several ocean-side marinas on the eastbound side of the highway. At the intersection with the southern terminus of CR 3 (South Wellwood Avenue), the name flips to East Montauk Highway as NY 27A continues northeast through Lindenhurst. At Park Avenue, the route passes south of a long strip mall along the north side of the roadway, crossing into the village of Babylon. Now in Babylon, the route switches back to West Montauk Highway once again, crossing an intersection with CR 96 (Great East Neck Road) and through the Bergen Point Golf Course. At Beachwood Drive, the route bends further towards the northeast, becoming a residential street through Babylon.
Now in the Deer Pen section of Babylon, NY 27A changes monikers to West Main Street, crossing into Argyle Park and an intersection with the eastern terminus of NY 109 (Little East Neck Road North). Bending a little to the east, NY 27A becomes a four-lane boulevard across the southern end of Argyle County Park. Crossing into downtown Babylon, NY 27A becomes a two-lane commercial street, flipping to East Main Street at Deer Park Avenue. After bending eastward, the route runs along the southern end of Hawleys Lake Park and the southern terminus of NY 231 (the Babylon–Northport Expressway). The interchange with NY 231 divides the eastbound and westbound lanes of NY 27A, which crossed into the town of Islip.
Now named Montauk Highway, NY 27A bends southeast past an intersection with the southern end of CR 82 (Higbie Lane). The route crosses east through Islip, passing south of Lake Capri, and bending northeast at Everdell Avenue. After passing Captree Elementary School, NY 27A enters exit RM2 of the Robert Moses Causeway, crossing into West Bay Shore on the other side of the parkway. At Lake View Road, the route changes monikers to South Country Road and passing north Gardiners County Park. Running northeast for a short distance through West Bay Shore, NY 27A winds past Southward Ho Country Club as a two-lane residential road. The route crosses into Brightwaters before passing back into Bay Shore.
In Bay Shore, NY 27A crosses an intersection with the southern terminus of CR 13A (Clinton Avenue) and soon CR 13 (Fifth Avenue). Now known as West Main Street, NY 27A crosses through downtown Islip, changing to East Main at Fourth Avenue. The route soon bends eastward past Orowoc Lake, passing several commercial businesses in both directions. The route intersects with Nassau Avenue in front of Islip Town Hall before intersecting with the southern terminus of NY 111 (Islip Avenue). Passing Brookwood Hill Park, the route crosses into East Islip, retaining the West Main Street name, remaining a two-lane commercial street. Crossing the southern terminus of CR 17 (Carelton Avenue), NY 27A changes names to East Main Street, crossing through the Country Village section of East Islip.
After Country Village, NY 27A bends northeast into exit 45 of the Heckscher State Parkway, a cloverleaf interchange and into the Bayard Cutting Arboretum State Park. Now in Great River, NY 27A bends northeast as Montauk Highway, junctioning with the eastern terminus of CR 50 (Union Boulevard). After crossing into North Great River, the route winds through the park as a two-lane roadway, paralleling the Montauk Branch of the Long Island Rail Road. Crossing into Central Islip, NY 27A enters exit 46 of NY 27 (the Sunrise Highway). At this interchange, NY 27A terminates, while CR 85 continues east along Montauk Highway.
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