Girls On the Go

Hit the Road for an Unforgettable Experience


Story and Photography by Lindsay Gifford

1,200 miles + 2 Besties + a cabin nestled on top of Brush Mountain + the Horse Capital of the World + Keeneland 2019 Spring Meet + hundreds of thoroughbred horses running hell for leather + a few bets = 1 Amazing Road Trip

When you look back at some of the most iconic movies it is not surprising that many of them have a common theme... a road trip! Whether it’s skipping school on Ferris Bueller’s Day Off, summering with National Lampoon’s Vacation, hitting Myrtle Beach with the girls from Shag, or adventuring with the guys in Road Trip, each one leads to unexpected adventures, memories and a ton of laughs. So why not decide to create your own memories and live out loud with your very own road trip?

Decide to do it. It’s easy to make excuses: “I’m too busy”—make time. A road trip doesn’t have to be a long one. “I have kids”—take the entire family, or load up your gal pals. “It’s too expensive to travel”—there are a ton of budget-friendly options like camping, packing food, or just taking the scenic routes and exploring the historic or wildlife trails. Not every trip has to involve an expensive theme park. “My car isn’t in great shape”—talk to an interested friend. Maybe, if they’ll drive you can foot the gas bill, or split the expense of a rental car. Just make sure you rent by the day, not the mile! Got some more excuses? I have answers, because I’m the same way. I have an incredibly demanding job that involves working a ton of hours to give you a beautiful magazine each month, and it’s easy for me to say “maybe next year.” As  I’ve gotten older, I’ve realized I don’t need to wait. I have to thank my friend Jess for suggesting we take a birthday trip each year. We’re on year two, and both adventures have been amazingly fun and memorable... and right before each one, I minorly freaked out and almost backed out because I was too busy—something I would’ve immensely regretted.

Kentucky or Bust: This past April, Jessica Caruso and I set our sights on the horse capital of the world—Lexington, KY—for our 2019 adventure. I’d traveled there once before during racing’s off-season and was anxious to witness the rush of watching thoroughbred racing at Keeneland Horse Park’s 2019 Spring Meet. My aunt and uncle recently purchased a cabin a couple hours from Lexington, so with that in mind, we decided to drive up and take advantage of the mountain air prior to the races.

On our first morning there, we set out for the races and took advantage of the ride to explore bloggers’ recommendations for a great restaurant for dinner. When we arrived at Keeneland Race Park, I was blown away by the sheer amount of people in their bowties and sundresses—no worries, we were dressed for the part. No horse racing experience is complete without betting, so the first thing we did was grab a stats book and engaged a “betologist,” who explained the ins and outs. Oh, and made a phone call to our friend who knows horse betting for a few tips—Beantown Boys, 2nd race, win - show.

We took our seats to witness our very first “and their off!” There’s no feeling like the thunder of hooves as the horses take off down the track. I just put my phone down and lived in the moment. Between races, we took our new betting knowledge to heart, comparing horses, placing a few bets and making sure our bet on Beantown Boys was all set. As the gates opened on the second race, we were jittery with excitement and cheering on our horse...he came around the bend in 3rd and at the last moment edged out the win by a nose—we won! After many more races, we headed out for our night adventure and enjoyed dinner at delicious Carson’s Food & Drink—complete with Kentucky bourbon. We sat at the bar, skipping the wait and meeting some fun people along the way.

The next day we started off with tours of Keeneland (behind-the-scenes) and a local horse-breeding farm. We learned all the ins and outs and history behind the thrilling races. Afterwards, we enjoyed brunch at Tally Ho—a Lexington tradition since 1971. Then the races lured us back, this time edging up by the track, to take some killer photos. We headed back to the cabin for the night and hit the road for our trip home the next morning, this time checking out some scenic overlooks along the way.

As we crossed into South Carolina, we decided to detour into Newberry so Jess could see my college and stop for a bite. Once we hit the road again and neared home, I realized we’d ridden nearly 18 hours in the car and never turned on the radio. What a blessing to find a friend who can enjoy chatting along the way, as well as the silent enjoyment of the scenic drive.  

Here are a few pointers to help you plan your own road trip. You will be #Adventuring and #LivingOutLoud in no time!

Have a Loose Plan:
>> Have a destination in mind, whether it’s as loose as a state, city, national park or event. Having an end goal will help you achieve the most out of your trip, without sacrificing too much time meandering.

>> Read up on where you’re going so you are mostly prepared. If you’re going to an event (like we were), purchase a ticket in advance in case they sell out. Be aware of the parking situation/entrances and what you can and cannot take in. Are coolers/tailgating a possibility? Am I required to carry a clear bag, or will my purse work? Can I bring my camera along? What does the seating look like? Are there refreshment options?

>> Think about your accommodations: Seek out your family and friends who are in the area, or check out hotel alternatives like AirBnB, Bed and Breakfasts or VRBOs.

>> Clean and organize your vehicle before the trip. This is my one unyielding rule. If you start organized, you’re more likely to enjoy your trip, spend less time looking for EVERYTHING during the trip and save time by not forgetting essential items.

>> Pack and Consolidate: Remember to pack light with easily movable luggage since you won’t likely stay in the same place each night. Chat with your co-tripper(s) so you don’t end up bringing four hair dryers and no shampoo. Pack your car with the ride in mind; put snacks and coolers in the back seat for easy access. Check the weather: Your road trip should take you out of your comfort zone, and that may mean some new weather patterns. Check your destination’s weather and pack appropriately. Don’t forget a poncho, it’s a small item that comes in very handy!

>> Bring cash. I know it seems foreign these days, but having available cash is a must. Whether you need it for parking, or the credit card machine is out at the gas station, it’s essential that you have cash to rely on. Remember, you aren’t just riding around the big city!

>> Be sure to bring along a set of printed directions and download a music playlist or podcast—you may not always have service. Also, pack an actual never know what treasures it will hold, like overlooks to enjoy.

>> Set a Budget: Think about budget-friendly options like packing food and drinks to avoid expensive fast food. With the money we saved by doing this we were able to take the horse tour I mentioned. Decide when you’ll eat out, and consider sharing so you get to enjoy two new things.

On the Road:
Talk to the local experts (like the betologist). Locals can often give you insight on places you shouldn’t miss out. When we decided on Kentucky, I texted all my friends who were familiar with the area and asked for suggestions. Also consider, reading travel blogs to brush up on the area so you get full experience, and look for tours that go behind-the-scenes.

>> Take advantage of the provided amenities at hotels, and grab a little extra fruit for a snack. If there are scenic overlooks, stop and enjoy lunch there. In fact, many places have scenic maps with alternative routes to check out.

>> Map it: When Jess and I were traveling, we tried out the app Waze to map our trip. I highly recommend it for your road trip! The app is a little more involved than your ordinary GPS. It provides directions, along with warnings of road hazards, policeman, the speed limit, traffic backups and alternative routes. And, it puts little “candies” along the map so you can collect achievements for how far you’ve traveled and gives points for helping warn fellow “Waze-rs” about hazards, traffic jams, accidents, etc. It offers a truly interactive experience.

>> Check in with your loved ones. This is especially true if you’re traveling rural roads and areas or hiking. There is often a lack of cell reception, and it’s important that someone know where you are staying. If you are without service, or don’t know the address, drop an iPhone “pin” to your loved one, or send them your “current location” so they know the vicinity. This can also come in very handy when parking! Mark it on your phone before leaving your car for an easy way back to your car.

>> Expect the Unexpected: It goes without saying... be aware of your surroundings. Be flexible. You may need to cancel a hotel reservation, or decide to extend your trip for a day. It’s okay, just go with the flow!

Capture the Memory...Then Experience it Firsthand:
Live in the moment. When I first arrived at races I wanted to capture everything on my phone, until I realized I was watching it through a screen... and I could do that at home. Capture it, then enjoy it.

Now, go out and do something you’ve never done before. Whether you’ve arranged your trip, or just want to wing it, there’s one thing you can’t plan for...your takeaway—how you’re going to feel about your experience and the memories you’ll bring home. One thing is true, as our souvenir shirts (we budgeted for) said, “Our hearts were racing at Keeneland.”

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