When you are ready to explore the Hamptons, you can drive, or bike, a loop to Southampton Village that will take you by scenic vistas, landmarks and some nice boutique shopping. With no stops this loop will take an hour or less, depending on the season and traffic.
Make your way to Montauk Highway (State Route 27) and travel east toward the main business district. The first stop to notice (and plan to return to) is the Hampton Bays Diner. This is has been a landmark for decades, and in the summer season is open late for a quick bite after a movie or a nearly midnight snack after an early club night. As you continue to travel east, you will find the E Day Spa on the northeast corner of Springville Road. This is a lovely salon and spa just perfect for a relaxing respite.
Another spot to notice in the Main Street area is Scotto's Italian Pork Store, on the right side of the road just before reaching Ponquoque Avenue. Scotto's is THE place to go for Italian specialties such as sausage for the grill back at Bayview Resort—especially if you struck out with the fishing pole.
Continue to travel east on Montauk Highway to find the Shinnecock Canal and the bridge that crosses it. If you turn left before the bridge on to Newtown Road, you will find a park area along the canal where you can watch the boats go by and enjoy some fishing. Travel further north and you will find a lovely bathing beach on Peconic Bay—much less intimidating than the Hamptons ocean beaches for inexperienced swimmers or young children.
Cross the bridge over the canal and continue east on Montauk Highway to find one of the prettiest water views in the Hamptons—especially if you are early enough for a sunrise. This view looks southeast across Shinnecock Bay to the Shinnecock Inlet the Atlantic Ocean beyond. Do take a moment to notice the Edgewater restaurant on the left side of the road, so you can plan to return for lunch or dinner with a side of a lovely view.
Montauk Highway starts to wind through Shinnecock Hills at this point, and you will travel along a tree-lined road with rolling hills toward Southampton College and Shinnecock Indian Nation Reservation. The college is now part of the SUNY system, offering a variety of programs, but specializing in marine programs, as a result of its proximity to the ocean. It's a beautiful campus with spectacular 360 degree views.
Just past Southampton College on the right side of the road you will find several businesses operated by members of the Shinnecock Indian Nation as this is the north border of their reservation. In addition to smoke shops, snack bars and cafes (with very good eats, by the way), you will also find their museum.
And then you will enter Southampton Village, home to some of the most expensive addresses in the world. Take care as you travel this part of Montauk Highway, also called Hill Street, as the 25 mph speed limited is strictly enforced. But that just gives you more time to enjoy the scenery. The hedgerows are tall, to provide the homeowners privacy, but the homes you can see are a delightful representation of late 19th/early 20th Century architecture mixed with mid-century moderns.
Just before you reach the business district, make note of the beautiful stone Basilica of the Sacred Hearts of Jesus and Mary. This Roman Catholic beauty has been the site of Kennedy weddings and special blessings for with other devout celebrities.
Once you reach the business district, you will find the Southampton Movie Theater, along with a broad array of restaurants, cafes and pubs for dining out. Name your cuisine and your price and you will likely find a suitable restaurant. However, before you stop for a bite to eat, look to the right as you travel east on Job's Lane (that's Job with the long "o" like the one in the Bible) and take in Agawam Park with the lake on the south side. There is a playground, a beautiful pavilion, picnic tables and a large grassy area to enjoy a rest and a snack. Municipal parking is conveniently adjacent to the park.
When you reach the stop light on the east end of Job's Lane, turn right to make your way along South Main Street for more Southampton mansions, along with the Thomas Halsey House—a museum building that is open for tours. Be sure to check the gardens!
But don't stop yet…keep going on South Main Street until you reach the end, and turn right on Gin Lane. Even more mansions await, if you can sneak a peek behind the hedgerows, but don't get too distracted. You will want to enjoy the shorebirds in Lake Agawam and the lovely vista across the lake, as you travel west on Gin Lane. You can make your way to the ocean here, but first travel just a bit west to the beautiful St. Andrew's Dune Church. This red chapel, with its luminous stained glass windows is a photographer's dream and a resilient historical building, having survived the Hurricane of 1938, and more recently Super Storm Sandy.
When you are finished admiring St. Andrews's, make your way back to the business district to park the car and stroll the sidewalks. You will find art galleries, boutiques, restaurants and even the historic Hildreth's Department Store—the oldest department store in America. It's a great place to browse and buy, especially if you are looking for something classically "Hamptons."
After your stroll along Main Street and Job's Lane, you can get back on the road and return to Bayview Resort on Montauk Highway, which is recommended if you biked it, but if you are in a vehicle, consider taking County Road 39 back to Hamptons Bays. This is a busy bypass route, with no shoulders (and therefore unsafe for biking), but it will bring you to some interesting landmarks—and if you are a fast food junkie, you will find McDonald's, Dunkin Donuts, 7-11 and Burger King within sight of each other.
To continue the loop without backtracking on Montauk Highway, navigate to North Sea Road and travel north to the intersection of County Road 39. Before you get too far on North Sea Road, consider stopping at Tate's Bake Shop for the best chocolate chip cookies you will ever have, especially if you like the crunchy kind.
After Tate's keep traveling north until you reach County Road 39 (just after McDonald's), and prepare to turn left to head west. There nothing too exciting to see until you get just west of Magee Street, and then you will find a driving range and snack bar open to the public, very near the Elks Lodge, which is the site of many summer fairs, carnivals, flea markets and the like. Check the schedule to see if anything fun is happening to coincide with your stay. Chances are you will find something…as there is nearly always something going on.
After the Elks Lodge and the driving range, keep on the lookout for the north side of the Southampton College campus (on the left), and on the right, the Shinnecock Hills Golf Club, which claims to be the first golf club in the US, and the first to admit women, which it did from its inception. You will not be allowed to play unless escorted by a member, but take the turn onto Tuckahoe Road anyway. The view from the top of the hill is gorgeous, with vistas north all the way to Peconic Bay, including the National Golf Course to the north of Shinnecock Hills and a windmill in the distance. This spot is a photographer's delight.
Travel north to the end of Tuckahoe Road, turn left and travel west on Sebonac Road. This will lead you along the waterfront, and pretty scenery until you come back to County Road 39 further west. Turn right and stay in the right lane, so you can bear off at the opening of Sunrise Highway (State Route 27), and travel back to Hampton Bays on North Road. If you are feeling peckish, you may like a stop at the Lobster Grille Inn, where you can treat yourself to a delicious meal—seafood or steak—and dine overlooking the creek.
As you continue west on North Road, get ready to bear off onto County Road 39A and Meschutt Beach. There is a snack bar, marina, nice beach on Peconic Bay, and plenty of parking. This marina is very near the Shinnecock Canal locks, so if you like admiring boats, there will be plenty to see.
When you are finished at Meschutt Beach and the canal locks, continue west on North Road until you reach Montauk Highway on the east side of the bridge that you crossed at the beginning of your journey. Turn right to head back to Hamptons Bays Main Street area and make your way back to the Bayview Resort.