Travel Guide: A Fall Weekend in the Hamptons

Over the summer, we snagged two flights to Long Island for about $13o round-trip (that Southwest Companion Pass came in big again!). I went to the Hamptons, Montauk specifically, for a few summers back in my twenties, but I wanted to revisit the area as a “grown-up.” Plus, Adam had never been and wanted to experience the much-talked about island for himself.

A FALL WEEKEND IN THE HAMPTONS

If you’ve ever been to the Hamptons during the summer, you know that it’s insane. I did the whole standing in line at Ruschmeyer’s, sipping on sunset rosé at Navy Beach, day drinking at Sloppy Tuna thing back in my heyday, but, for a low-key, just-the-two-of-us trip, escaping to the Hamptons in early fall seemed like a lovely (and, hopefully, less expensive!) way to spend a weekend.

We lucked out, of course, with the weather — sunny and high-50s, low-60s — for two of the days we were there. And, the leaves up in New York are a few weeks ahead of those in DC, so we got a much-anticipated dose of autumnal charm.

 

fall in the hamptons - southampton

fall in the hamptons - southampton

fall in the hamptons - southampton - flying point beach

fall in the hamptons - milk pail hamptons - pumpkin patch hamptons

HOW TO GET TO THE HAMPTONS

Surprisingly, the Hamptons are not terribly easy to get to if you’re trying to use ground transportation. From DC, driving takes about 7 hours (I’ve done it…it’s not ideal) or you can bus or train to NYC and then hop on the Jitney out to the island.

However, as much as I will stand by my belief that flying to NYC doesn’t make sense, it does make sense to fly to the Hamptons if you plan on going just for a few days. You may be wondering, “The Hamptons have an airport?!” Well, not exactly. There’s an airport in nearby Islip on Long Island, so we flew into ISP — a quick, 44-minute flight from BWI* — and then rented a car. From the airport, it’s about 45 minutes to Southampton, where we were staying. Super easy.

A travel tip: we always try to book our trips Saturday to Monday to save on airfare! We arrived midday Saturday and left Monday late afternoon. 

* Yes, I know…BWI. Adam and I actually fly out of BWI frequently and it’s closer than most DC people realize, plus, parking is only $8/day. For us, BWI is a 40-minute drive, while DCA is 15-ish minutes, and Dulles…ugh, Dulles is FAR.

 

fall in the hamptons - windmill hamptons - easthampton windmill

fall in the hamptons - sag harbor

fall in the hamptons - sag harbor

fall in the hamptons - sag harbor

WHERE TO STAY AND HOW TO GET AROUND

I’ll have an entire post dedicated to our hotel next week (y’all know how I feel about accommodations — my standards are high and I hate to be uncomfortable, so I love sharing good finds with you!), but, in the meantime, here’s the short synopsis. We stayed at the Southampton Inn, which is right in downtown Southampton. Seriously, you can’t stay in a more convenient spot. We were able to walk into town each morning and, had we had the inclination, we could have biked to the beach.

While I’m sure you can do without a car if you’re in the Hamptons solely for a weekend of summer frolicking, I do think it’s wise to have a way to get around if you’re there for a quiet weekend getaway. The island isn’t big, but nothing is particularly close. From Southampton out to Montauk is about an hour, with towns including Easthampton, Wainscott, and Sag Harbor in between. We rented a car at ISP and were glad to have an easy way to zip between town, vineyard, and beach.

 

fall in the hamptons - southampton

fall in the hamptons - southampton - golden pear cafe

fall in the hamptons - southampton

fall in the hamptons - sag harbor

WHERE TO EAT AND DRINK IN THE HAMPTONS

We ate well while in the Hamptons — one of our goals was to indulge in seafood and I’m still dreaming about the multiple lobster rolls I had on our trip. I’ll walk you through everywhere we went from our first meal to our last before heading home.

  • The Seafood Shop: The first stop once we arrived, this fish market in Wainscott has just a handful of seats outside where you can enjoy a lobster roll, clam chowder, or maybe a crabcake on a nice day. Stop in Wainscott Main Wine & Spirits while you wait to grab a bottle of wine for the evening.
  • Bridgehampton Candy Kitchen: Y’all know I love an old-fashion ice cream shop, so it’s no surprise we popped in here.
  • Claude’s at Southampton Inn: After a long day, we were happy to dine at the Southampton Inn’s restaurant. Whenever a hotel has a great restaurant, I always like to take advantage of at least one meal there — particularly if I’m tuckered out from a long day traveling. The chef at Claude’s has been cooking homemade Italian meals for over 35 years and you are doing yourself a disservice if you don’t get the fettuccine alfredo.
  • Golden Pear Cafe: A classic in the Hamptons, this local chain serves delicious pastries, breakfast items, light lunches, and coffee.
  • Tate’s Bakeshop: I don’t think there’s anyone in the U.S. who hasn’t had a Tate’s Bakeshop chocolate chip cookie at this point, but we had to make a pilgrimage to the original, right?!
  • Lucharito’s: We took a boat ride with Adam’s aunt and uncle from Sag Harbor to this lively Greenport Mexican restaurant. The duck nachos and the coconut shrimp tacos are both home runs, particularly on a crisp fall day.
  • Sag Town Coffee: With a slight chill in the air on an overcast day, this uber-hip coffee shop made for an excellent place to grab a cortado or flat white (I didn’t check to see if their coffee was pour-over, but, come on, it for sure is).
  • Tutto Il Giorno: The Southampton outpost of this Manhattan Italian restaurant offers an amazing Sunday night dinner — $55 for a family-style dinner to serve two with appetizer, pasta, main course, and 2 glasses of wine.
  • Four Oaks Cafe and Juice Bar: Because I was feeling like I needed something healthy after 2 days of indulging, I grabbed an acai bowl for breakfast at this vegan-friendly spot.
  • The Lobster Roll aka Lunch: Since 1965, this seafood operation on Montauk Highway has been dishing up lobster rolls to locals and celebs alike. Of course, we got the lobster roll, but we also ordered puffer fish served in an upscale fishstick form (yes, it was delicious).

A word of advice: if you spend a fall weekend in the Hamptons, always check ahead of time to make sure the restaurant is open. Most places we had on our itinerary were open, but there were a handful with limited hours or that were closed entirely.

 

fall in the hamptons - wainscott hamptons - seafood shop hamptons - lobster roll hamptons

fall in the hamptons - wainscott hamptons - seafood shop hamptons - lobster roll hamptons

fall in the hamptons - lunch hamptons - seafood shop hamptons - lobster roll hamptons

fall in the hamptons - lunch hamptons - seafood shop hamptons - lobster roll hamptons

WHAT TO DO DURING A FALL WEEKEND IN THE HAMPTONS

We jam-packed our itinerary from start to finish while we were in the Hamptons. I mean, when you’re presented with a gorgeous fall weekend and no to-do list, why not take full advantage of it, right?! We arrived in Southampton around 1 PM and were out in Montauk for the evening — yes, it was a drive, but Adam wanted the full experience. Here’s the rundown of what we did from Saturday midday through Monday afternoon.

  • Flying Point Beach: We couldn’t take a trip to the beach without actually visiting the beach, right? This beach, located right in Southampton, was surprisingly busy with people out enjoying the gorgeous fall day. Some were walking along the water, some had brought a chair and a book, and everyone seemed to be basking in the autumn sun.
  • Channing Daughters Vineyard: We’ll put aside the guy who I accidentally opened the bathroom door on and instead focus on the wine tasting experience. The vineyard was buzzy, but not so crazy that we weren’t able to grab a comfortable spot to do a tasting. I didn’t love the wines here, but it’s a great place to spend an afternoon sipping on a tasting and people watching.
  • Wölffer Estate Vineyard: You’ve seen it on every blogger’s Instagram, but Wölffer Estate lives up to the hype. The space is absolutely stunning — which is probably why it was mobbed when we went there. We couldn’t get a table or a spot at the bar, so we decided to move on. Hint: you can also visit the Wine Stand nearby…the groups of girls walking in their best fall fashions, hats and boots included, from the vineyard to the wine stand was more than I could count.
  • Montauk Lighthouse: I have now twice visited the Montauk Lighthouse when it’s been closed…womp, womp. However, it’s still a cool place to walk around — the views of the lighthouse from the rocky coastline are impressive.
  • Montauk Brewing Company: Adam wanted to make sure we stopped by Montauk Brewing Company for the beer. I was there for the eavesdropping on the group of twentysomethings next to us. They don’t do tastings on the weekend, but I was into the Pumpkin Ale, while Adam held on to summer with the Watermelon.
  • Boating: We were fortunate to spend an afternoon out on the water with Adam’s aunt and uncle who live in Sag Harbor. You can’t beat a day spent boating, particularly on a cool fall day.
  • Duck Walk Vineyards: I’m a fruit wine fan, so I was all in on this vineyard’s tasting with multiple fruit wines, a port, and other sweet options. We were here in the pouring rain (it rained just for a bit on Sunday afternoon!), so we had the place to ourselves. Don’t worry, the woman working the tasting room kept us entertained.
  • Parrish Art Museum: A small museum, but one worth visiting, we went during the incredible Helen Frankenthaler exhibit. Seeing her large scale work side-by-side with photographs of the artists who were traipsing around the Hamptons during her day was fascinating. Also, the sleek, rustic architecture of the building itself is striking against the landscape.
  • Pumpkin Patches: We didn’t go to one of the many pumpkin patches, but we did stop by Milk Pail for cider donuts. That totally counts, right?!

 

fall in the hamptons - montauk lighthouse

fall in the hamptons - montauk lighthouse

fall in the hamptons - sag harbor

fall in the hamptons - parrish art museum

fall in the hamptons - parrish art museum

fall in the hamptons - channing daughters winery

A FEW FINAL NOTES ON A FALL WEEKEND IN THE HAMPTONS

While the Hamptons have a reputation for being ridiculously expensive, if you go in the off-season, you won’t find prices to be any different than those in any big city. Plus, going in the fall lets you avoid the crowds and lines that warm summer days bring to the island. If you have any questions about how we planned our fall weekend in the Hamptons, be sure to give me a shout!

 

fall in the hamptons - tate's bake shop southampton

fall in the hamptons - the milk pail

 

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