Main Street in Highlands, NC has been the bustling heart of the community for 150 years. As you stroll along today, you can almost hear the echoes of its early days when a handful of houses, stores, inns, and churches dotted the then-dirt roads. Over time, this modest beginning has grown into a vibrant shopping district, home to both historic businesses and new favorites.
In the early days, a few key businesses served as the foundation for Highlands’ growth. Baxter White’s general store, near today’s Town Square, was one of the earliest landmarks, doubling as the post office and the town's only shop during its first three years, providing essentials to the fledgling community. By the 1880s, Main Street had grown to include several more stores, including H.M. Bascom’s hardware shop (this was located at corner of W. Main Street & N.4th Street) and James Rideout’s Granite Store, which later served as the foundation for the Edwards Hotel (part of current-day’s Old Edwards Inn & Spa). One of the oldest and most beloved shops on Main Street is Wit’s End. Opened in 1940 by Margaret Southard Young, Wit’s End has remained a family-run business for 85 years. Originally offering porcelain and home accessories, the store has evolved to specialize in classic women’s apparel. Generations of families have made shopping at Wit’s End a tradition, maintaining its cherished place in the community.
As the town grew, so did the number of businesses. Reeves Hardware opened its doors in 1944, providing tools, hard-ware, and home supplies, and remains a cornerstone of downtown. The store moved to its current location at 3rd and W. Main Street in 1970 to meet growing demand.
While some historic businesses have transformed over the years, their presence is still felt. The former Galax Theater, located on W. Main Street just east of today’s Town Square, was once the town’s premier movie house from 1948 until its closing several decades later. While the theater no longer shows films, its historic sign remains, proudly displayed above the storefronts of Annawear, The Christmas Tree, and Natural Selection. These shops offer an eclectic mix of women’s clothing, year-round holiday finds, and nature-centered gifts and trinkets, respectively, blending Highlands' past with present-day commerce.
On E. Main Street, The Dry Sink has been a Highlands staple for just over 50 years. After outgrowing its original space on S.4th Street, the store moved to its current location in 1980, a building that once housed Highlands Hardware (1940-57) and even a bowling alley. The store has since expanded, offering a wide range of goods, from kitchenware and candles to gifts and seasonal decor. Known for its exceptional customer service, The Dry Sink is a must-visit for locals and visitors.
Another Main Street icon, Highland Hiker, has been outfitting outdoor enthusiasts for decades. Originally called the Happy Hiker, the store was located on Church Street and purchased in 1982 by David and Carol Wilkes, who moved the store to Main Street and transformed it into what is now a thriving family business. With multiple locations, including their flagship log cabin store and a dedicated shoe shop, Highland Hiker offers everything from outdoor gear to curated apparel. The log cabin store holds much history. Built in the 1930s, it was originally the summer home of Dr. E.E. Reinke, a Vanderbilt University professor and the first director of the Highlands Biological Station. The Wilkes’ commitment to customer service and love for the outdoors has made Highland Hiker a staple in both Highlands and Cashiers and remains a go-to destination.
Development has shaped the look of Main Street as well. From the early dirt roads to today’s brick sidewalks, the charm of Highlands has been carefully maintained through thoughtful growth. The addition of shopping centers like Wright Square, which expanded businesses along W. Main Street in 1984, and The Falls on Main, which expanded businesses along E. Main Street in 2000, has helped expand the retail footprint, making room for newer businesses while ensuring that Highlands' unique character is preserved. Located across from Hudson Library, The Falls on Main occupies the former site of Highlands’ co-founder Samuel T. Kelsey’s home, which was built in 1875 and burned down in 1976.
At its core, Main Street is more than just a place to shop—it’s a living history of Highlands. Each business, whether rooted in the past or newly established, tells a story of 150 years of growth, resilience, and a shared love for this mountain town. Whether you’re visiting a local gallery, dining at a fine restaurant, or browsing shops, Main Street offers a blend of past and present that makes every visit feel timeless.