road trip — Travel — Stephanie Rollens

Long time no see! I know it’s been a minute, but I won't get into a litany of excuses for this procrastination. I’m glad to be back here writing about the spots I’ve visited so far this summer, so without further ado, enjoy!

Because I live so close, I try to head out to Montauk and the Hamptons as much as I can during the summer. Whether it’s for a weekend or just a day trip, I’ve learned that half the fun really is getting there, and some of my favorite road trip memories have been on Montauk Highway, either speeding down the empty road if we’re lucky, or more often than not, stuck in miles and miles of stop and go traffic. I usually stay and hang out the most in Montauk, but there are a couple of pit stops I love making along the way.

On one of my most recent trips out east, my friend Shelby and I were determined to stop at Wolffer Estate Vineyard for a glass of wine and a bite to eat. I’ve fallen in love with their rosé, but have never actually gotten to see the vineyard. You can imagine the deep, dark hole of despair my heart sunk into when we found out it was closed for a wedding that day. Boo.

Luckily, Wolffer has a small shop and eatery right off Rt. 27 simply called “The Wine Stand”, and it turned out to be exactly what we wanted. As you walk up to their small shop right up against the vines, you pass the Rosé Drive Thru outside - their “adult” take on a lemonade stand. It’s ADORABLE, but you actually can’t buy anything from them out there. Instead, you have racks upon racks of wine, cider, and even their new rosé gin to choose from inside.

After picking up a bottle of their rosé table wine to bring home, we ordered two glasses of their new Dry Rosé Cider and sat out on their patio next to the vineyard. Of course, it was only 1 PM so I ended up leaving with a nasty sunburn, but all in all, so worth it.

It really is a great place to relax and get the whole “Wolffer experience” without going up the road to the main estate itself. Quick tip - summer weddings are BIG at Wolffer, so if you plan on doing a tour or visiting their tasting room, definitely call ahead and check if it’s even open.

If you’re a seafood lover like me, our next stop is something of a pilgrimage: The Lobster Roll in Amagansett. Recognizable by its gigantic “LUNCH” sign nestled atop the tiny restaurant in the middle of nowhere, some say it’s where the dish by the same name was pioneered.

The iconic restaurant is a casual eatery with some seating indoors, a covered outdoor area, and an open patio in the back. While some places in the Hamptons and Montauk have become posh - and dare I say pretentious at times - this holds onto the same cozy, no-frills feel that I remember from visits out east when I was a little kid.

There are paper menus, plastic cups, dogs sitting at the patio table next to you, and the smell of the most delicious, fresh local fare wafting from the kitchen behind you. I usually get a lobster roll when I come here, but I decided to change it up and get the fried oyster po'boy which did not disappoint.

To say this place is beloved wouldn’t even really scratch the surface, and it is, in my opinion, a national treasure. Also in case you were wondering, they serve lobster rolls both hot and cold here - the cold is a traditional lobster salad with mayo, veggies and seasonings, and the hot is simply steamed lobster with melted butter drizzled on. Both are incredible, so, you know, go at least twice. Okay I think I’m done fangirling now.

This is more of a no-brainer for any drive through the country, but I really wanted to give farm stands an honorable mention before wrapping up my favorite Hamptons/Montauk pit stops. I love the way they can sneak up on you, and most often have different products every single day - you know, actual farm fresh food (what a concept right???). Aside from great fruits and veggies, I’ve scored some delicious jams, honey, plants and pies depending on the time of year and location. My favorite by far is definitely Bhumi Farms in Amagansett.

Not only is it arguably the most instagram-able stand ever (I mean just LOOK AT IT), but they always have a wide variety of produce and the most gorgeous sunflowers! I’m also a big believer in supporting small businesses, and visiting family farms and farm stands like this is a great way to do that.

The road out to Montauk has so many great things to see whether they’re scenic, historical, or just fun, and I love exploring more every time I drive out there. Which ones did I miss, and which ones are your favorites? Let me know, I’d love to do a Part II!