Saratoga Springs: High Stakes, Horses, and History

Horses on Saratoga's Historic Race Track.

It’s fair to say that I had zero idea of what to expect headed into a weekend at Saratoga Springs, a hub of thoroughbred horse racing, mineral baths, and a world class performing arts center. My last trip to this Gilded Age destination was over 20 years ago on the way to a friend’s wedding in Lake Placid. On that trip, we stayed on Saratoga Lake and explored the quaint downtown area and made a point to go to the Saratoga battlefield, which played a key role in the American Revolutionary War.

I was told by my sister to pack two dresses for the races at the track and didn’t have time to investigate anything else, as I’m still relatively new at my current position. I imagined the races at Ascot, which I have seen in magazines like Town & Country or even Julia Roberts in Pretty Woman at the polo match using her heels to stomp the divots back into the ground.

With this mindset, I set off on a flight to Albany and was enlightened by my seatmate on what I was going to experience. I had no idea that our trip coincided with the Travers Stakes, which is one of the most storied races in the country. In fact, it’s been a tradition for 156 years, which is a few years older than the Preakness Stakes, which turned 150 years old in 2025. It’s known as America’s oldest and most prestigious race outside of the Triple Crown and typically draws up to 50,000 people more than doubling the population of the surrounding area.

The gentleman regaled me with stories of his time as a bartender during the event, where he made up to $10,000 in a weekend. So, it was with a bit more information that I set off with my sister for the historical town, which once offered a sophisticated retreat from the summer heat of New York City, solidifying its reputation as a social and recreational playground for the powerful and rich. 

In some ways, this hasn’t changed. The shear number of Bentley’s, Maybachs, and priceless historic Mercedes on display reminded one that you were in the company of people who have achieved remarkable success or at the very least inherited it.

After a breakfast at Sweet Mimi’s, where we waited for a while for a table at the popular and delicious establishment and I nearly passed out (true story) we set off to check into our hotel and dress for the day of festivities. I wore a navy Hobbs dress from the UK with pretty buttons and fine details along with a borrowed fascinator that matched my sister.

Trying my fascinator on for size with Kath!

Fascinators, a formal hairpiece for women, are big business in Saratoga and everyone is encouraged to wear one with several stores offering one more spectacular than the next.

Upon arrival at the racetrack, we posed for some photos and set out for the paddock bar which was protected from the heat of the sun and had screens showing the day’s races. The cast of characters at this particular bar was like something out of a movie. In fact, Carly Simon sang about one of them infamously in “You’re so Vain,” back in the 1970s. On the left, there was a 90-year-old man wearing a shirt adorned with sushi placing bets and helping our group of “young ladies” figure out which horses to choose for our bets. To the right, there was a group of thirty-year-olds out for a weekend on the town and reliving their fun high school days. And in the middle was our large group of 10 or more people celebrating a friend’s retirement and enjoying time spent together. But the real show were the women in their various apparatuses. I literally stood in the same spot for a few hours and never tired of watching the fashion show, which was quite grand.

In the evening, as the sun began to wane, we headed over to Siro’s, an iconic restaurant that has stood for 75 years, serving up a scene that includes a Veuve Clicquot bar, live music and a pianist inside the historic setting who entertains the boisterous crowd. A short walk away was our friends’ Airbnb where we cooled our heels before setting out for an evening on the town. With same dress and fascinator off, we wandered to the Ice House, to hear a band regaling us with tunes from the 1990s and then over to the Wild Horse, to rinse and repeat.

After a few hours of enjoying conversations that made us cry from laughing we went back to our hotel and crashed for the night only to get up and do it all over again. This time, I had a fashion show of sorts trying on the floral and apparently all wrong dress I brought from a boutique in Annapolis along with a green flowy number my sister loaned me and the eventual black halter dress which I wore with my pink fascinator. Although comfort clothes are more my speed, it was definitely the right move after clocking the attire of many at the track on the big day.

What else did we learn from a visit to this legendary town on its most popular weekend?

Find Accommodations Early: My sister is a pro as she has worked in upstate New York for several years now over two positions and knows what to expect. We stayed in a serviceable Holiday Inn right downtown that was within walking distance of restaurants and the racetrack. Even so, we still took Ubers when needed.

• Pack well: I didn’t bring the right attire. I think the first day I was fine with my elegant dress and hair attire in cinq with the others in attendance, but you may want to gauge what to anticipate based on weather and comfort. Most importantly, bring footwear you can comfortably wear for many hours. At least on this note, I was on target with my sandals.

• Bring cash: You will need it for covers at some of the bars with live music, for tips and for betting if that’s something you are interested in doing. I ended up betting $20 and won $86, so that was a pretty happy moment.

• Have a backup plan for restaurants: If you come to Travers weekend, it is likely you will not get a table. For us, we ended up eating one big meal in the morning and we coasted on it the entire day. If you can’t do that and are renting Airbnb, make sure you have some snacks and other food on hand. Our friend made chicken parm and it was perfection.

• Pace yourself: I had a few glasses of bubbly along with several glasses of water. When it is sunny as it was the weekend we attended, it may cause you to feel exhausted. Hydrate frequently and make sure you stay out of the sun for periods of time.

• Mind the yellowjackets: With an influx of people comes the presence of yellowjackets, which I mention as I spent a lot of time keeping them at bay all over town and at the racetrack. They were a nuisance that you need to live with to enjoy an outing, but if asked to eat outside or inside, I would heartily recommend staying indoors after experiencing their aggressiveness on a few occasions!

Other Things to Do:

Explore the Historic Saratoga Spa State Park: My sister and I enjoyed strolling in this beautiful park with natural springs, the Roosevelt Baths and Spa, and the world-renowned Saratoga Performing Arts Center.

Yaddo: If you are looking for a quiet contemplative place to read a book, go no further than the gardens at Yaddo, which is a sanctuary for artists at all creative stages. I’m thrilled that places like this still exist and enjoy that there is a wonderful place offering residences for people working in choreography, film, literature, painting, and performance art, to name a few of the people you might find here.

Places to Eat/Drink:

Triangle Diner: This is an old school diner offering generous portions of classic breakfast offerings in throwback digs. I learned that people in this region enjoy griddled muffins, which is something you don’t see in the South too often. My favorite was blueberry with jam and butter along with a vegetable omelet and fruit.

Bocage Champagne Bar: We fell in love with this intimate champagne bar offering tastings right on Phila Street steps from downtown. There are glasses from Ukraine, France, Greece, and Italy along with the typical splurges.

9 Maple Avenue: Thanks to some sleuthing from our friend who was in search of an establishment with excellent jazz, we came upon this excellent lounge in an 1880s era speakeasy pouring hundreds of single malts and martinis with a beautiful backdrop of a rich mahogany bar.

Lagos by Saratoga Lake.

Shopping

Miss Scarlett’s: If you are looking for that perfect fascinator, a t-shirt, or fun gift for someone go no further than Miss Scarlett’s which is a fun shop right on Phila Avenue in downtown Saratoga.

Overland: One of the few freestanding stores in the U.S., this gorgeous shop contains modern, artisan crafted sheepskin products including jackets, boots, and hats to wear when it starts to get a little bit cooler in the Fall and Winter months.

Northshire Bookstore: I love a good independent bookstore, and this one fits the bill with helpful staff and a carefully curated library of selections.

All in all, although I came with no plans or understanding of what the weekend would entail or how things would go, I had a really nice time, made some new friends, enjoyed a storied tradition from the past and came away with some great memories. If you should find yourself in the Albany area, I highly recommend making the trip to Saratoga!