Summer 2023 Itineraries


By Laurie Paolicelli

Southern Village.

Now that all of our graduates have graduated, Memorial Day has come and gone, and the mercury is doing its best to climb, summer has officially come to Orange County. It would take a dozen summers to experience all we have to offer, but here are a few suggestions. Because some businesses close on Mondays and Tuesdays, suggested itineraries are organized by day of the week. Mix and match! For even more ideas,


Park in downtown Chapel Hill at the Mallette Lot and walk to the Purple Bowl for a tasty breakfast, then drop in next door to the Visitors Center for brochures, and a photo with James Taylor and Michael Jordan. This is the best place to begin your journey through Orange County!

If you’re a walker, head west to Carrboro. Check out Carr Mill Mall, and just wander around this beautiful, friendly town.

Back at your car, drive to the Carolina Basketball Museum. The interactive exhibits and rich history of Tobacco Road basketball will fascinate you.

Dinner. Dinner is trickier on Monday nights but not impossible. Some favorites on Monday nights include 411, Med Deli, Carolina Brewery, Venable Carrboro and Osteria George near Whole Foods.


Park in the Wallace Deck, have breakfast at Sutton’s and then take the U-Bus (it’s free!) for a loop around campus. Download the free App of the University’s icons to inform your ride.

Back in your car drive to the Chapel Hill Community Center Park, just down the road. Walk through the rose garden and then down Bolin Creek Trail.

Top off your day with a trip to the North Carolina Botanical Garden.

The Carrboro Farmers Market is a colorful way to spend some time while visiting.


Park in the Wallace Deck again.

Stroll over to the Carolina Coffee Shop, the oldest restaurant in North Carolina offering Southern cuisine, a full bar, and, yes, coffee.

The Ackland Art Museum is around the corner. It houses over 18,000 works of art, including European masterworks, 20th century, contemporary art and much more.

The Carrboro Farmers Market is open 3:00 pm – 6:00 pm. Located at 301 West Main Street, vendors sell a wide selection of the highest quality locally grown foods.

Drive-over to mid-town for Sally Mack, a specialty store, Flyleaf Books, and a cold drink at The Root Cellar Café.

While at Flyleaf, pick-up a book by a local author. Some favorites include: Daniel Wallace, Sarah Dessen, Jill McCorkle, and part-time resident, John Grisham.

Whitehall Antiques, Chapel Hill, NC.


Start your day at Café Driade.

Next door is a popular antiques venue, Whitehall Antiques, specializing in period 18th and 19th century English and Country French furniture, fine art, silver, porcelain, and lighting.

Enjoy lunch at the Carolina Inn Hotel. Valet park.

Before getting back in your car, walk across the street and get your photo taken by the Old Well, the most iconic sight on campus.

Nothing gets the night going like live music. Cat’s Cradle in Carrboro is a legendary venue where you can see both indie and nationally known artists. Local 506, as its name implies, is a spot that is great for enjoying local acts.


Hillsborough is a small town with a big history. The downtown historic district, listed on the National Register of Historic Places, features more than 100 homes, churches, and buildings from the 18th and 19th centuries. Today, Hillsborough is a haven for artists and writers.

Park in the public deck next to Weaver Street Market.

Stroll the RiverWalk, a paved, accessible, urban greenway that stretches about 2 miles along the Eno River.

The Historic Occoneechee Speedway Trail offers an easy, three-mile stroll that includes the only dirt speedway remaining from NASCAR’s inaugural 1949 season.

For lunch, hit the main drag, Churton Street. Treat yourself to the many fine and fun restaurants in downtown Hillsborough.

The Wooden Nickel, Hillsborough.

If it’s the Last Friday, then you hit the jackpot in Hillsborough. Last Fridays & the Art Walk a FREE town-wide celebration of art & community, hosted by the Hillsborough Arts Council.

Do not leave Hillsborough without seeing The Colonial Inn, an 1838 landmark hotel lovingly restored in 2020.

Saturday or Sunday

Walk the Carrboro Farmers Market for local produce, bakery, crafts. Open Saturdays.

Free walking tours are offered in Chapel Hill. Enjoy a leisurely walk around campus and the main downtown district.

Catch a show in the theater at the Morehead Planetarium, home to astronomy classes and NASA training programs.

Hit a brewpub at one of the dozens of micro-brews. If a traditional high-ball cocktail is more your style, visit The Crunkleton.

For a fun dinner, try Imbibe, a Cajun joint in the heart of downtown Chapel Hill.

Half Muffalata at Imbibe, Chapel Hill.

Enjoy a sheep herding tour or walking tour of farmlands and vineyards at Union Grove Farm, founded in 2002 by fifth generation farmer Greg Bohlen who is committed to regenerative agriculture and completion of a Chapel Hill vineyard.

Sign up here:

Union Grove Farms.

Sunday Concert on the Village Green in Southern Village is a great place to hear local and regional bands. It’s free, but BYOB (bring your own blanket) Or chairs.

Again, use these suggestions as a mere starting point for your adventures in Orange County. And watch this space for more recommendations as the summer proceeds!

Add these events to your itinerary:

Friday walking tours at Visitors Center, 308 W. Franklin Street

Fridays on the Front Porch, Carolina Inn

First ever massive public art installations, UPROAR

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