Collect your SUV at Long Island MacArthur Airport in Ronkonkoma, allowing about an hour for the rental desk, paperwork, vehicle inspection, and loading bags. Before leaving, photograph every side of the vehicle, the wheels, windshield, fuel gauge, and mileage; confirm the return instructions and whether toll charges are handled through the rental company. The airport rental center is close to the terminals, but allow extra time if several flights arrive together. Once you have the keys, set navigation before driving—Long Island traffic can become surprisingly slow even on short east–west routes.
Drive roughly 15–20 minutes south to Connetquot River State Park Preserve in Oakdale. The preserve is a lovely first outing with the SUV: quiet pine and oak woods, sandy trails, and glimpses of freshwater around the historic South Side Sportsmen’s Club grounds. Plan about two hours for an easy walk, wearing comfortable shoes and carrying water; trails can be uneven, and ticks are a consideration in September, so check clothing afterward. The preserve generally operates during daylight hours, with seasonal hours and parking policies worth checking before departure; arrive well before closing because there is little nearby once the gates shut.
Continue about 15 minutes east to The Oar Steak & Seafood Grille on the Patchogue waterfront for dinner. Expect approximately $30–$60 per person before drinks and gratuity, with seafood, steaks, and a relaxed marina setting; reservations are sensible for a Sunday evening, especially if you want a table near the water. Afterward, spend around 90 minutes wandering Patchogue Village—follow Main Street toward the harbor for independent shops, cafés, and a livelier first-night atmosphere than the airport area. Street parking and public lots are available, but read signs carefully and avoid moving the SUV after dinner if anyone is drinking; the village is compact enough to explore on foot.
Start at Sagtikos Manor in West Bay Shore, ideally arriving around 9:30 a.m. for a guided tour and time to wander the grounds; allow about 1½ hours. This 18th-century estate is one of the area’s quieter historic gems, with period rooms and a distinctly old-Long-Island atmosphere. Tour schedules can be limited or seasonal, so confirm the day’s opening time before setting out; admission is typically modest, often around $10–$15. From central Islip, the drive is roughly 15–20 minutes via local roads and Montauk Highway, with easy on-site parking.
Continue west toward Robert Moses State Park Field 5, allowing about 25–35 minutes depending on traffic. You’ll need a New York State Parks vehicle-use fee—generally around $10, though rates and payment procedures can change—and September is much calmer than midsummer. Walk the broad Atlantic beach, bring water and sun protection, and keep your vehicle pass handy if you plan to leave and re-enter. From Field 5, the route toward the Fire Island Lighthouse follows the boardwalk and sandy trails; wear sturdy shoes, as the walk is more comfortable than attempting it in sandals.
Spend the early afternoon at the Fire Island Lighthouse, allowing roughly 1½ hours for the lighthouse grounds, museum displays, and—if available—the climb up the tower. The lighthouse itself is reached from the Field 5 parking area by a walk of about 1.5 miles each way, so budget several hours door to door rather than treating it as a quick stop. Tower access can depend on weather, staffing, and current preservation work, and there may be a small admission fee; even when climbing is unavailable, the shoreline views and surrounding maritime forest are worthwhile. Leave enough time to return to your SUV before dusk, when the boardwalk and beach paths become less clearly marked.
For dinner, drive back to Tellers: An American Chophouse in Islip, a polished restaurant set in a former bank building. A reservation is sensible, especially for a prime evening seating; expect approximately $50–$90 per person before drinks, tax, and tip. Order something substantial after the beach—steakhouse classics and seafood are the natural choices—and take a few minutes to admire the restored banking details inside. Since you’ll have had a full day outdoors, this is best treated as the final stop rather than adding another outing afterward.
Begin at Heckscher State Park in East Islip, arriving around 9:00 a.m. for a relaxed two-hour walk along the Great South Bay waterfront. The park’s paved and packed-gravel paths are easy in an SUV, and the open shoreline, salt-marsh views, and beach areas feel especially peaceful before midday. Bring water and a light layer—the waterfront can be breezy even in September. The vehicle entrance fee is typically charged seasonally, so allow roughly $8–$10, and keep your receipt if you plan to come and go. From there, it’s about a 10-minute drive west to Bayard Cutting Arboretum State Park via Montauk Highway; parking is straightforward, but arrive before late morning for the quietest garden paths.
Spend roughly two hours at Bayard Cutting Arboretum State Park, wandering through its formal plantings, woodland trails, and views toward the Connetquot River. The grounds are best enjoyed slowly rather than as a checklist, with plenty of benches and shady stretches. Admission is generally around $10 per vehicle, though seasonal hours and fees can change; check the park’s official listing before setting out. For lunch, drive about 10 minutes east to Irish Coffee Pub in East Islip, a long-standing neighborhood restaurant known for generous portions of shepherd’s pie, burgers, sandwiches, and other American-Irish comfort food. Plan on $20–$35 per person and about an hour; calling ahead is sensible if you arrive during the Sunday lunch rush.
After lunch, take the SUV east toward the Atlantis Marine World Aquarium area in Riverhead, allowing approximately 35–45 minutes via Montauk Highway depending on traffic. The destination is more than the aquarium itself: spend time along the Peconic River waterfront, browse the nearby shops and attractions, and enjoy the working-harbor atmosphere. If you decide to enter the aquarium, check current admission and closing times online before leaving East Islip, as ticket prices and hours vary by season. Otherwise, two hours is enough for a pleasant waterfront visit without turning the day into a tightly scheduled attraction crawl. Expect heavier traffic on Montauk Highway near Riverhead, particularly late afternoon, so leave a little flexibility for the drive back.
Drive east to Long Island Aquarium in Riverhead, about 35–45 minutes from central Islip via the Long Island Expressway and Route 58, depending on traffic. Aim to arrive around opening, typically 10 a.m.; confirm the September 2026 schedule before leaving, as hours and ticket prices can change. Set aside roughly 2½ hours for the indoor galleries, sea-lion and penguin habitats, and interactive exhibits. General admission is usually in the $40–$50 range for adults, with parking available on-site. The aquarium is a good rainy-day stop, but it is also worth allowing a little outdoor time around the Peconic River afterward.
Around midday, head to the Riverhead Farmers’ Market, if its seasonal schedule lines up with your visit. It is generally a short drive from the aquarium, though market days and hours should be checked in advance because this is not a daily year-round stop. Give yourself about an hour to browse local produce, baked goods, preserves, and prepared foods; it is an easy place to assemble a casual lunch rather than committing to a full restaurant meal. Keep the SUV cool if you buy anything perishable, and leave a little flexibility in case the market is operating on a reduced late-season schedule.
Continue west on Route 25 toward Mattituck, allowing about 20–25 minutes. Spend the afternoon around the village and North Fork Community Theatre, checking the performance calendar and curtain time ahead of arrival; local productions commonly run about two hours, with evening shows often making the most sense. Street parking and small lots can fill before a popular performance, so arrive 20–30 minutes early. Before the show, this is a pleasant stretch for an unhurried walk along Love Lane and the surrounding village streets. Finish at Love Lane Kitchen, where seasonal North Fork ingredients anchor a relaxed farm-to-table dinner. Expect roughly $30–$55 per person before drinks and tip, and reserve ahead if your theatre ticket gives you a fixed dinner window. Afterward, the drive back toward Islip is typically 35–45 minutes via the LIE; avoid lingering too late if you want an easier return through evening traffic.
Head east toward the North Fork for Hallockville Museum Farm, roughly a 40–50 minute drive from Islip via the Long Island Expressway and Route 25. Aim for a late-morning arrival, around 10:00 or 10:30 a.m.; the museum’s hours and guided-tour schedule can vary by season, so check ahead before setting out. Allow about 1½ hours to explore the preserved farm buildings, tools, and exhibits on Long Island’s agricultural history. Parking is generally straightforward, and the SUV is useful on the rural roads, though expect narrow lanes and active farm traffic around Riverhead.
Continue west a few minutes to Paumanok Vineyards in Aquebogue for a relaxed tasting around noon. A flight generally costs about $20–$30, with additional glasses or bottles available; reserve ahead if you want a table, particularly on a September weekend. Give yourself about 1½ hours to enjoy the vineyard setting without rushing. From there, drive approximately 10–15 minutes to Jamesport Farm Brewery, where you can sample farmhouse ales and seasonal releases in a working agricultural setting. Tastings and pours commonly run about $8–$14, and the outdoor areas are casual—bring a light layer for the late-afternoon breeze and check the brewery’s event calendar, since live music can make parking busier.
Finish at The Preston House & Hotel in Riverhead, only a short drive from the brewery. Book dinner for around 6:30 or 7:00 p.m.; the restaurant is known for polished, seasonal cooking and a more refined atmosphere than the afternoon stops. Plan on roughly $60–$100 per person before drinks and tip. If you arrive early, take a quiet walk around downtown Riverhead before your reservation, but leave plenty of time for the drive and avoid drinking enough to affect the return journey—use a rideshare or arrange a designated driver if needed.
Drive from Islip to Orient Beach State Park on the North Fork, allowing about 1¼–1½ hours via the Long Island Expressway east to Riverhead, then Route 25 and Route 25A. Leave around 8:00 a.m. to make the most of the quieter roads and arrive near opening; September hours and the vehicle-use fee can change, so check the park’s current schedule before setting out. Follow signs for the beach parking area, bring water and a light layer, and spend roughly two hours walking the shoreline, dunes, and maritime forest. The park is pleasantly undeveloped, but facilities are limited compared with Long Island’s busier beaches.
Continue west along Route 25A and Old Country Road to Orient Country Store, a short drive from the park. Pick up sandwiches, salads, baked goods, or other picnic provisions—budget about $15–$30 per person—and eat casually before browsing the shelves of local and specialty products. From there, drive about 10 minutes to Lavender by the Bay in East Marion. Allow 1½ hours for the fragrant fields, seasonal photo spots, and farm shop; bloom timing varies, and late September can be quieter after peak flowering, so check admission, hours, and field conditions online before going. Wear shoes suitable for uneven ground and avoid visiting immediately after heavy rain.
Finish in Greenport, about 10–15 minutes west, with coffee at Aldo’s Coffee Company. The compact village is easy to explore on foot from the café, so park once and take a relaxed stroll along Front Street and the waterfront; allow around $8–$18 per person for drinks and a snack. For dinner, walk or make the short drive to Noah’s, where creative seafood and seasonal North Fork dishes typically run about $45–$75 per person before drinks and gratuity. Reservations are wise for a September evening, and Greenport parking can become tight around dinner—arrive 20–30 minutes early rather than circling the village.
Drive from Islip to Greenport Harbor Brewing Company in Greenport, allowing roughly 45–60 minutes via the Long Island Expressway and Route 25, with extra time if North Fork traffic builds. Arrive around 11:30 a.m. for an easy start: sample a flight of local beers, order something casual if available, and settle into the relaxed brewery atmosphere for about 1½ hours. Designate a driver—the tastings add up—and check the September 2026 opening hours before setting out. Afterward, leave the SUV parked and stroll around Greenport village rather than moving it; street parking can be limited on weekends, and the waterfront is much more enjoyable on foot.
Walk to the East End Seaport Museum, allowing about 1½ hours for its exhibits on Long Island’s whaling, fishing, and boatbuilding traditions, as well as the lighthouse displays. The museum is compact, so this pairs nicely with a slow wander along the harbor and nearby marinas. Expect admission to be roughly $10–$20 per adult, with seasonal hours sometimes varying; confirm the day’s schedule before visiting. Keep an eye on the clock for your next appointment, then drive to the Shelter Island Kayak Tours meeting point—typically a short ferry crossing from Greenport followed by a brief island drive. The North Ferry from Greenport generally takes about 10 minutes, but lines can grow on weekends; arrive 30–45 minutes early and verify the operator’s launch location and reservation instructions.
Spend about two hours with Shelter Island Kayak Tours, paddling calm coves and protected coastal water if wind and tides cooperate. September is often ideal—less crowded and pleasantly warm—but bring water shoes, sunscreen, a dry bag, and a change of clothes. Guided tours commonly cost around $75–$120 per person, and conditions can lead to route changes or cancellation, so reserve ahead and avoid drinking before the excursion. After returning the kayaks, allow time to rinse off and drive across Shelter Island to The Pridwin for dinner. Book a table around sunset and expect approximately $45–$80 per person before drinks and gratuity; the waterfront setting is the main attraction, so request an outdoor or harbor-facing table when making the reservation. The last ferry back to the North Fork may be less frequent in the evening, so if you are returning to Islip tonight, check the South Ferry schedule before dinner; otherwise, enjoy the sunset without rushing.
Leave Islip around 7:45 a.m. for the North Ferry terminal in Greenport, allowing roughly 50–70 minutes via the Long Island Expressway and Route 25; weekend North Fork traffic can slow the final stretch. The ferry crossing to Shelter Island takes about 10 minutes, but arrive 20–30 minutes early because vehicles board in line and departures are first-come, first-served. Expect a modest vehicle-and-driver fare, with current prices and sailing times best checked before leaving. Once across, drive to Mashomack Preserve for about 2½ hours on its marked trails through woodland, freshwater ponds, salt marsh, and shoreline. Wear sturdy shoes, bring water and bug spray, and check trail conditions and access hours before setting out—there are few services once you enter the preserve.
After the hike, continue to the Shelter Island Historical Society, usually a short drive from the preserve. Spend about an hour with the island’s local-history exhibits and historic buildings; opening days and hours can be limited outside the summer peak, so verify the September schedule before committing to the ferry crossing. For lunch, keep it simple at The Island Mermaid, a casual waterfront spot in Shelter Island Heights, or pick up something to-go and eat near the harbor if the weather is pleasant. Leave enough time to return to the North Ferry terminal for the crossing back to Greenport—vehicle queues can build on Sunday afternoons, and the crossing itself is about 10 minutes.
From Greenport, drive west to Brix & Rye in Riverhead, generally 25–35 minutes via Route 25 depending on traffic. Settle in for cocktails and small plates in the polished, relaxed bar setting; budget approximately $30–$60 per person before gratuity, more if you order several drinks. Because seating can fill on a weekend evening, a reservation or early arrival is sensible. Afterward, return to Islip via Route 25 and the Long Island Expressway, allowing roughly 45–60 minutes and watching for heavier traffic near Riverhead and the western North Fork.
Leave Islip around 8:30 a.m. for the South Fork, allowing roughly 50–70 minutes to reach Parrish Art Museum in Water Mill. Take Sunrise Highway east, then Route 27; weekday traffic is usually manageable, but the final stretch through the Hamptons can be slow. The museum generally opens at 11 a.m., so check the September 2026 schedule and reserve admission if required. Allow about two hours for its modern and contemporary Long Island collection, and use the on-site parking rather than trying to park along the busy roadside.
From Parrish Art Museum, it is about 15 minutes east to LongHouse Reserve in East Hampton. This peaceful sculpture garden is best enjoyed slowly—wear comfortable shoes, bring water, and expect grassy or uneven paths. Seasonal hours can be limited, so confirm opening times before driving over; plan on roughly two hours. Afterward, continue into East Hampton Village for a pastry or casual lunch at Carissa’s The Bakery, where $15–$30 per person is a sensible estimate. The bakery can be busy at lunchtime, and seating is limited, so takeaway is often the easiest option. Spend the later afternoon at Main Beach, a short drive from the village: September is quieter than midsummer, but check beach-access and parking rules, as permits and lifeguard coverage may still apply. Bring a towel and avoid leaving valuables in the SUV.
For dinner, head to Nick & Toni’s in East Hampton, preferably with a reservation made well ahead; this celebrated seasonal restaurant is popular even after the summer rush. Expect about $60–$100 per person before drinks and tip. Since the day’s stops are spread along Route 27, allow extra time between the beach and dinner, and keep the SUV parked once you reach the village rather than attempting to move it repeatedly.
Leave Islip around 7:00 a.m. for Montauk Point State Park, allowing roughly 1½–2 hours via Sunrise Highway and Route 27. The final approach through Montauk is scenic but can slow down, especially on a Sunday, so an early start is worthwhile. Parking near the lighthouse is generally straightforward in the morning, though September access and fees can vary; bring a light jacket, as the point is often windy. Spend about two hours on the coastal paths, taking in the bluffs and open Atlantic views before visiting Montauk Point Lighthouse Museum late in the morning. The lighthouse grounds and museum typically open in the daytime, but confirm the September 2026 schedule before driving out; admission is usually modest, with separate access or seasonal restrictions possible for climbing the tower.
Drive west about 35–40 minutes to The Lobster Roll in Amagansett, the roadside seafood institution locals simply call “Lobster Roll.” Arrive before the main lunch rush—around 11:30 a.m. or 12:00 p.m.—for the best chance of avoiding a long wait. Expect roughly $25–$50 per person, depending on whether you choose the famous lobster roll, fried seafood, or a lighter plate. After lunch, continue a few minutes west to Napeague State Park, where a relaxed 1½-hour walk gives you both ocean and bay scenery along the narrow strip of land between them. Check parking signage carefully and bring water; facilities can be limited outside the busier summer season.
Return to Amagansett for an early dinner or a little downtime before heading to The Stephen Talkhouse, one of the East End’s most intimate live-music rooms. Check the event calendar in advance—showtimes, cover charges, and age policies vary, and popular acts can sell out. Arrive 30–45 minutes before the listed start, since the room is compact and standing space fills quickly. If there is no suitable performance scheduled, use the evening for a casual walk around Amagansett’s village center and leave Montauk before the late-night crowds; otherwise, plan to stay about two hours and drive back to Islip afterward, allowing roughly 1½ hours on Route 27.
Start around 8:00 a.m. and drive west from Islip to Sands Point Preserve in Port Washington, allowing roughly 55–75 minutes via the Long Island Expressway, depending on weekday traffic. The preserve is a worthwhile change of scenery from central Long Island: former Gold Coast estates, wooded paths, formal gardens, and open views across Long Island Sound. Allow about 2½ hours, including one mansion tour if available and a shoreline walk. Check the September opening schedule before setting out; admission and parking are typically modest, but mansion access may require a separate fee or timed tour. Wear comfortable shoes, and bring water—the grounds are more expansive than they first appear.
Continue about 15–20 minutes to Nassau County Museum of Art in Roslyn Harbor, set within the former Frick estate. Plan around 1½ hours for the galleries and sculpture garden; exhibitions change, and the grounds are especially pleasant for a short walk between rooms. Admission is generally in the roughly $15–$20 range for adults, with hours often concentrated during daytime and early afternoon, so verify the calendar before leaving Sands Point Preserve. For lunch, drive into Roslyn and settle at The Bryant, a polished neighborhood restaurant where lunch or an early dinner usually runs about $30–$60 per person before drinks and tip. Its location is convenient for a relaxed meal rather than a rushed roadside stop, and you can take a brief walk around the village afterward.
In the late afternoon, drive about 20 minutes east to Planting Fields Arboretum State Historic Park in Oyster Bay. Give yourself roughly two hours for the formal gardens, greenhouse areas, and estate grounds; late September is a lovely time for the changing foliage and softer light. Parking is generally available on-site, while tours of the historic buildings may have separate hours or fees. Finish with dinner at Harbor House in Cold Spring Harbor, about 15–20 minutes away, aiming for an early reservation around 6:30 p.m.; waterfront tables are limited, and evening service can fill quickly. Expect approximately $35–$65 per person before drinks and gratuity. Allow 45–60 minutes to return to Islip afterward, using local roads toward Route 25A and then the Long Island Expressway; after dinner, check traffic before choosing the most direct route.
Allow about an hour for the SUV return at Long Island MacArthur Airport in Ronkonkoma. Before entering the return area, refill the tank at a nearby station on Veterans Memorial Highway or Lakeland Avenue—airport fuel prices are usually higher. Remove belongings, photograph the mileage, fuel gauge, bodywork, wheels, and interior, then allow extra time for the agent’s inspection and shuttle or walk to the terminal. If your flight is later in the day, returning around 9:00–9:30 a.m. keeps the rest of the morning comfortable; confirm the rental company’s after-hours procedure if returning outside desk hours.
After the drop-off, take a short taxi or rideshare west to The LakeHouse in Bay Shore, generally 15–20 minutes depending on traffic. Request a table overlooking the Great South Bay if available, and plan on roughly $30–$60 per person for brunch or lunch before drinks. It is a pleasant final meal rather than a rushed airport stop, but check the day’s service hours and reserve ahead—waterfront tables are limited, particularly on weekends.
Walk off lunch at Bay Shore Marina, following the waterfront for about an hour and enjoying views across the bay toward Fire Island. From there, drive north to Islip Grange Park, roughly 10–15 minutes away. This is a simple, quiet final stop with open lawn and local neighborhood atmosphere; allow about an hour if your flight timing permits. Keep an eye on the clock, since traffic around Sunrise Highway and the airport approaches can become unpredictable, and leave Islip Grange Park with at least two hours before a domestic departure.