Visiting Southampton, New York in the Fall

Did you know that “The Hamptons” are a collection of small villages and hamlets that includes: East Hampton, Bridgehampton, Southampton, Westhampton,┬áSagaponack, Sag Harbor, Watermill and a few others.

You might spot celebrities like Brooke Shields, Rachael Ray, Howard Stern or Jennifer Lopez, who all own properties in the Hamptons. If you like star gazing and want to find out where some of your favorite celebrities live in the Hamptons check out this Hamptons Celebrity Homes Map

The reason so many celebrities take refuge in The Hamptons is that you will not find any paparazzi, strip malls, or event a larger grocery store and definitely not a Walmart. What you will find are close-knit communities of small business owners, boutiques, cafes, and events that gather people together. Community is often lost in our society and we all yearn for it. The Hamptons towns and villages have that sense of purpose. The Hamptons might seem to be the place just for the very rich and famous but we felt right at home when we visited.

Since we had never been to Southampton we decided to stay in a well-known Inn called the Southampton Inn. The Southampton Inn is conveniently located just out of the main town on 91 Hill Street. It is quite affordable at around $199 a night during the week, off-peak. That’s reasonable for this area are you will not find many chain hotels in the towns. There are some outside of town about 15 to 20 minutes away. When you stay in the Hamptons you are looking for the entire experience so staying at a local Inn or Bed & Breakfast fulfills that need.

Southampton Inn

The first day on our trip, we ventured into the town and our first stop was a lovely coffee shop and cafe at 99 Main Street called The Golden Pear Cafe. The Golden Pear Cafe offers breakfast, pastries, quiche, sandwiches, salads, and great coffee anytime of day. When you open the door of The Pear Cafe you immediately feel welcomed by the smell of fresh pastries and coffee. The Pear Cafe is the perfect stop for coffee and we enjoyed it so much we came back the next day for lunch.

The Golden Pear Southampton

The Golden Pear Southampton

There are so many things to do in Southampton that cost little or no money. This can definitely be an affordable trip. Window shopping is a favorite, people watching, driving around and “house gawking” and walking by the ocean are some of our favorite things to do and they don’t cost a dime. Of course, once you are in some of the shops you may want to open your wallet but that is completely optional.

Main Street, Southampton NY

You will find lots of people out walking their dogs. Make sure to stop by Ralph’s Barber shop on Main Street and say hello to Buddy, the resident Yellow Lab. He might even do a trick for you.

Buddy, Yellow Lab

Walking down Main Street you will walk past small boutiques, dress shops, a cheese shop, galleries, the local barber and Hildreth’s Home Goods Department Store. Hildreth’s (51 Main Street) is “America’s oldest store” and has been around since 1842. This is where you want to go for celebrity spotting and to get inside information from the locals about the town. Celebrities often shop at Hildreth’s because it has everything – furniture, children’s, bed and bath, tabletop, outdoor, home decor, gifts, notions like yarn and fabric and even a toy store.

Hildreth's Southampton

If you are looking for a quick bite to take back to your hotel , stop in The Village Gourmet Cheese Shoppe for on-the-go cheese platters, Smoothies, or an Espresso.

Southampton NY Shopping

Once you have spent the day in town, make reservations for dinner at 75 Main. 75 Main has been recognized as the number 1 Italian restaurant in The Hamptons. When the weather is nice, you will find guests dining outside and if you are eating inside, they open the doors to let the fresh air in.

75 Main Southampton, New York Review

If the weather is good you must drive down to Cooper’s Beach on Meadow Lane. Parking is free in the Fall after Labor day and you can spend an afternoon walking on the beach, picking up shells, walking the dog, or watching the waves come in.

Cooper's Beach Southampton

Cooper's Beach Southampton

Driving past Cooper Beach you will see beautiful homes lining both sides of the streets. Some of the ornate gates are just as beautiful as the houses and you might want to stop and wonder who lives there.

Southampton Estates

Southampton Estates

Southampton Estates

Munn Point boardwalk is another place you should stop and visit. It’s free to park and walk on the boardwalk. There is a small parking lot in front and it is just a short drive from Cooper’s Beach at 881 Meadow Lane. “Munn Point is named for Orson D. Munn, a Southampton Village trustee from 1967 to 1985. It has a boardwalk with benches that reaches out to Shinnecock Bay and is a popular destination for birdwatchers.”

Munn Point Southampton

Munn Point Southampton

Munn Point Southampton

With so much to see and do, a trip to Southampton, New York, must be on your itinerary for the Fall.

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