Small towns often have the biggest surprises. At least, that’s what I’ve experienced on my road trips across the country. I never pass a small town because I’m always certain a fantastic local eatery, unique arts and crafts shop, or intriguing museum is just waiting to be discovered. That’s why I made a point to visit the 9 small towns, and 1 small city, in South Carolina’s Olde English District.
I will admit a lot of the small towns are best kept for day trip visits, but a few of them were worthy of an extended weekend getaway. Rock Hill, the one city on this list, makes an excellent place to stay with all the towns on this list a day trip away.
This list of small towns, and one small city, to visit is listed in order from smallest in population to largest. Which of these will you explore next? Leave me a comment below!
Ridgeway – Population 319
Settled in the 1700s, Ridgeway was a booming rail town at one point and connected to the world via telegraph lines before the Civil War. Today, the picturesque southern town closes shop before 5 p.m. on weekdays, and nothing is open on Sunday, so you’ll have to time a visit just right to take advantage of the local shopping and dining.
The Palmer Street Market is the place to find new items like home décor and clothing. The Cotton Yard Market is the place for antiquing with a constantly shifting selection of eclectic items. Over the Top Boutique, the only clothing store in town, has a selection of fine clothing and jewelry.
Olde Town Hall Restaurant & Pub is a good place to get something to eat. The casual restaurant serves gourmet pizzas, burgers, and signature steaks in the historic building that once served as the town hall. My recommendation for lunch in Ridgeway is the charming and peaceful Laura’s Tea Room. The main attraction is Afternoon Tea or High Tea, but I visited for lunch where I enjoyed a bowl of creamy potato soup and grilled pimento cheese sandwich.
READ MORE: Road Trip Through the Olde English District of South Carolina
Winnsboro – Population 3,550
During the winter of 1780, the small town of Winnsboro became the unwilling host of Lord Cornwallis. After suffering defeats during his southern campaign, the British general spent a few months living in a gorgeous house in town. The current owners of that house began the Cornwallis House Tea Company, a beautiful little shop in town for getting a light lunch and tea.
The Fairfield County Museum is an intriguing place to explore and learn about the local history of the town. Do a little shopping at the Abba Sweet Treats & Gift Boutique while walking around the gorgeous downtown area. I think the most interesting attraction in town is the South Carolina Railroad Museum. Take a tour of various freight and passenger cars, go aboard an old steam locomotive, or schedule a ride on the Rockton & Rion Excursion, a 10-mile journey to a neighboring town.
READ MORE: 40 Travel Photos to Inspire You to Visit South Carolina’s Olde English District
Chester – Population 5,607
I was quite surprised upon entering Chester to suddenly find myself driving up a rather steep hill. Downtown Chester is nicknamed the “Hill District” because of its position on a hill in the countryside. The Chester County Historical Society was an interesting museum located inside the old county jail (and yes, you can still visit the jail cells on the top floor). The Chester County Transportation Museum, located inside an old warehouse along the railroad, had a small collection of antique vehicles, firetrucks, and a school bus.
Just outside of town was Chester State Park, one of more than a dozen state parks in South Carolina built by the Civilian Conservation Corps. Centered around a 160-acre lake the park includes a small campground, a couple of disc golf courses, and a nature trail around the lake.
Cheraw – Population 5,851
The quaint town of Cheraw has seen a lot of history pass through since its founding as a trading post in 1740. In March of 1865, General Sherman made camp in Cheraw for several days during his campaign. Surprisingly, he ordered his men to leave the town intact when he moved north.
One of the biggest events in Cheraw is the annual South Carolina Jazz Festival which celebrates the life and achievements of Cheraw native Dizzy Gillespie. A memorial to the jazz icon stands in the center of town across the street from the Lyceum Museum, a one-room museum filled with artifacts from the town’s history. Old Saint David’s Church is a gorgeous place to explore with more Civil War history, but pay close attention to the people buried in the cemetery.
Just outside of town is Cheraw State Park, one of only two state parks in South Carolina with a golf course. The rustic cabins are a great place to spend a night or two while enjoying the boardwalk trail around Lake Juniper.
Cheraw Chamber of Commerce Visitor Center 221 Market Street, Cheraw, SC | 843-537-7681 | http://www.cherawchamber.com
National Park Week 2024
Learn about the annual celebration of the National Park System and read my travel guides to national park units across the country.
Camden – Population 6,838
Founded in 1730, Camden is the oldest remaining inland town in South Carolina. In 1780, Lord Cornwallis marched into the small trading town with 2,500 British troops and seized the town for almost a year. The Historic Camden Revolutionary War Site brings The Battle of Camden to life each year with a spectacular reenactment. During the rest of the year, visitors can explore the historic homes and buildings on the property and take guided tours.
Did you know Camden is the site of the Springdale Race Course for steeplechase racing? I had no idea horse racing even existed in South Carolina! The National Steeplechase Museum, the only museum of its kind in the country, displays the history of steeplechase racing along with an amazing trophy room.
I began each day in Camden with a walk along Broadway Street, the main street through downtown, for lots of shopping and dining. Each morning I stopped at Books on Broad where I could enjoy a delicious coffee while browsing their book selection. The Broad Street Market had a few shops to explore with eclectic items; interestingly the entrance passes through Salud Mexican Kitchen & Tequila Lounge where I had dinner that night. The next night I visited Steeplechase Sports Bar & Grill. It looked pretty much like any other sports bar, but the food was amazing and a step above typical “grill” food.
York – Population 7,736
Take a drive down Congress Street through the York Historic District and you’re almost guaranteed to fall in love with this small town. Once upon a time, the town of Yorkville was an important stagecoach hub for travel through the South Carolina Upcountry. Today, York is an off-the-beaten-path destination for an afternoon of fun.
Begin with a walk along the tree-lined streets and browse through the windows of antique stores. The historic Sylvia Theatre would be a great place to catch a matinee, comedy show, or enjoy some live music. The Garden Café is one of the most exclusive places in the region; reservations are highly recommended for dinner. But don’t mistake this for a hoity-toity joint, it’s just that their food is really, really good and people will drive for hours just to dine there. After dinner you might try heading over to Rainbow Donuts to see if they still have some of the delicious doughnuts baked fresh every day.
My favorite thing to do in York is to spend a couple hours hanging out at Windy Hill Orchard and Cider Mill. Fritz and Catherine Gusmer wanted to start a business that could be operated by the entire family. With a passion for anything to do with apples, the couple founded the orchard so they could make apple cider doughnuts, apple pies, and hard apple cider. The best time to visit Windy Hill Orchard is mid-August through the end of October when the apples are ready to pick, live music fills the air on the weekends, and fresh baked goods are ready to go.
Union – Population 8,393
Union is the most remote small town in the Olde English District, but that means you’ll just have to drive a little further to get there when you visit. Start with the Union County Museum to learn about the history of the area dating back to its founding in 1749. Take a walk down Main Street through the historic district and take note of the retro light fixtures lining the street. Head down to the Union County Library to admire the gorgeous architecture of the Carnegie Library, recently voted as the Best Small Library in America.
Did You Know?
By the late 1800s, steel tycoon Andrew Carnegie was one of the wealthiest men in the world. He was also one of the greatest philanthropists in history. His greatest contribution to society was the Carnegie Library System.
From 1883-1929 a total of 1,689 Carnegie Libraries were built across the United States, mostly in rural areas where no library existed before. Carnegie only provided the funds for building the library while the local governments had to commit to funding the operation and providing access to anyone.
Take a detour out of town to visit Rose Hill Plantation State Historic Site. Take a guided tour of one of the best-preserved plantation homes in the state. During the tour you’ll learn about the plantation owner William H. Gist, the governor of South Carolina who pushed for secession after Abraham Lincoln was reelected president of the United States.
Lancaster – Population 9,175
Lancaster is one of two towns on this road trip featuring a courthouse designed by architect Robert Mills, the Charlestonian who also designed the Washington Monument (the other Mills courthouse is in Camden). Today, the bottom floor of the restored courthouse is the Lancaster County Museum, an excellent place to begin the exploration of this small town.
While driving through town you might notice several names revolving around red roses, including Red Rose Park on Main Street. During the mid-1400s, the War of the Roses were a series of civil wars fought in England between the House of Lancaster and House of York. The symbol for the House of Lancaster was a red rose. When settlements in the colonies were named after the noble house, the red rose would become a symbol of the town.
Nearby Andrew Jackson State Park is located near where the president was born in the Waxhaws region of the Carolinas. Along with a lake for fishing, boating, and kayaking, the park also includes a fantastic museum exploring Jackson’s childhood and political career.
READ MORE: Discover a President’s Boyhood at Andrew Jackson State Park in Lancaster, South Carolina
Fort Mill – Population 10,811
Just 15 miles south of Charlotte, the quaint town of Fort Mill is a welcome break from the concrete jungle of the big city with a return to rolling hills, trees, and a slow southern pace. Founded in 1873, the town is named after an old British fort built to protect Catawba Indians and Webb’s Mill.
Start with a visit to the Fort Mill History Museum to learn about the Catawba Indians who once called this area home, the founding of the town in the late 1800s, and the booming textile industry that is still a major employer today. Take a walk down Main Street for window shopping or hop inside to do some actual shopping. Pay a visit to Amor Artis Brewing to sample their craft beer and then head next door to The Improper Pig for a delicious meal.
The hottest place in town to visit is the PuckerButt Pepper Company. In 2013, owner Ed Currie was awarded the Guinness World Records title for World’s Hottest Chili. The Carolina Reaper, a perfect name if ever one existed, is grown in this area of the Carolinas and measures a whopping 1.64 million Scoville Heat Units. Hop inside this small store on Main Street to sample that chili and many others and decide what you want to take home.
Rock Hill – Population 74,309
The one bonafide city in the Olde English District, Rock Hill has become a major hub for tourism and adventure just thirty minutes south of Charlotte. Youth sports tournaments are held in the city almost every weekend throughout the year, and in 2020 the Charlotte Panthers moved their headquarters south of the border.
Rock Hill has everything a big city needs with all the charms of southern hospitality. Newsstand Record & Books is one of the few vinyl record shops I have come across in my travels. Just down the street is Friends Books on Main, a used bookstore selling books from the local library. The Main Street Bottle Company was a wonderful place to get a drink and then shop for some local craft beer in six packs.
READ MORE: 10 Awesome Things to Do in Rock Hill, South Carolina
When you get hungry, I have the perfect plan for you. It starts with dinner. Choose between wood fired pizza at Millstone Pizza and Taproom or gourmet burgers from Flipside Restaurant; they are next door to each other if that makes the decision easier. Then, walk down the street to get a sweet treat at Amelie’s French Bakery & Cafe. It’s the perfect way to end any day in Rock Hill.
If you visit Rock Hill on a third Friday from May through October, you’ll likely find the streets surrounding Fountain Park closed off, filled with food trucks and tasting tents, and packed with locals having a good time. Food Truck Friday is one of my favorite events held in the city and almost makes it worth a weekend visit just for the local food and craft beer.
Visit York County 130 East Main Street, Rock Hill, SC | 803-329-5200 | www.visityorkcounty.com
