15 Things to Do in Pittsboro, NC

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Pittsboro has a lot of offer, making it the perfect day trip from anywhere in the Triangle.  From antique shops to natural escapes to upscale dinners and laidback bevs, you might just have to turn your adventure into an overnight stay!  Check out my original post here with Offline Media.


French Connections Shop: It’s hard to drive into Pittsboro and not make this your first stop. The eclectic decor out front is enough to make you turn your car right into the driveway. French Connections is full of gorgeous fabric, linens, home decor and jewelry, and all products are ethically traded and are sourced from Mexico, France and 20 African countries. It’s easy to get lost in all the beauty, and the owners are very kind and fascinating.

15 Things to Do in Pittsboro

Circle City Books & Music: This store caught my attention because of the book mural on the side of the building. After checking out the titles painted on the side, I realized that all the books are written by North Carolina authors! Circle City is unique and has a great collection of tapes, records and books. You can spend hours in the shop browsing the collection and I definitely recommend stopping in.

15 Things to Do in Pittsboro

Chatham Home: This adorable little shop upcycles furniture and boasts a wide variety of locally made products. It is the perfect place to pick up an interesting gift (especially with the holidays looming!) and the staff is incredibly knowledgeable about where products come from and their back story.  

15 Things to Do in Pittsboro


Vino!!: This wine shop has an incredible selection of beer and wine, plus other gifts like wine glasses and cigars. I was impressed with the wide variety of beer and wine, but also by how affordable the selection was! It’s definitely a gem to have in this downtown. Bonus, there are wine tastings on Fridays from 5-7p!

15 Things to Do in Pittsboro


Blue Dot Coffee: This is the perfect spot to stop and grab a cup of coffee and a light snack before exploring. The lemon poppyseed muffin is my pick here! There are unique artwork and gifts throughout the coffee shop that are worth a peek for that one friend who’s got it all!

The Mod: The Mod has the coolest outdoor patio and an awesome menu to go with it! The artichoke woodfired pizza is my go-to here, but the sandwiches are delicious as well. There’s a perfect view of the courthouse from the patio, making it a nice break stop in the downtown.

15 Things to Do in Pittsboro


Allen & Son BBQ: For my BBQ lovers, you have to go to Allen & Son for a sandwich and hushpuppies. My husband and I differ on our opinions of BBQ—he likes pulled pork and I will not eat anything other than chopped BBQ. Allen & Son offers the best of both worlds of North Carolina style BBQ if your house is divided like ours.

15 Things to Do in Pittsboro

The Granary: If you’re heading to Fearrington for the afternoon, this is a great place to stop for lunch or dinner. It’s a Southern comfort menu with English flair. My favorite was the shrimp and avocado salad offered at lunch! And the wine list and full bar offer a delicious complement to the food menu.

15 Things to Do in Pittsboro

Oakleaf: The Oakleaf is in a very hip part of Pittsboro and is housed in the old silk labor factory.  This converted space offers beautifully exposed beams and brick walls. It is a farm-to-table restaurant open for lunch and dinner with an eclectic menu.  The crab meat pasta is a favorite of mine.  The menu does change depending on what’s available.  If you go, I may suggest trying the chef’s spontaneous menu.  That will be what I do on my next trip!


Fearrington House: The environment in the Fearrington House Restaurant is upscale, yet comfortable. The bar offers a rich selection of wines and cocktails, and there are beautiful fireplaces in most of the dining rooms. This is a farm-to-fork restaurant that’s also Green Certified (the only one in the US recognized by AAA Five Diamond & Forbes Five Star restaurants to hold this honor). The ingredients are sourced from local farms, in addition to the gardens on the grounds.  The experience is spectacular and worth a trip for dinner.

15 Things to Do in Pittsboro

City Tap: City Tap is awesome for a little snack or beverage break while strolling through town. The pretzels—baked by Guglhupf, a German bakery in Durham—are a must-try!  

15 Things to Do in Pittsboro


Chatham County Courthouse: This awesome courthouse is a showstopper in the center of the town. You’ll find it in the center of a traffic circle (hence the town nickname “Circle City!”) and boasts Victorian era architecture.  The first floor of the courthouse contains a history museum of Chatham County.

Haw River: This was perhaps my favorite part of my day trip. The Haw River is gorgeous and the pedestrian bridge in Pittsboro is great for checking out local graffiti art and breathtaking views of the river. This is an absolute must!

15 Things to Do in Pittsboro

Fearrington Village: There is so much to do in so little time at Fearrington! You can relax with a spa visit, stroll through the shops, grab a cup of coffee at The Goat, say hi to the Beltie goats and cows or just relax at the Roast Beer Garden. The grounds also offer lots of trails to explore and gardens to take in. It is the perfect getaway retreat in the middle of the Triangle.



Fearrington House Inn: The Fearrington House Inn is a gorgeous space in the center of a former dairy farm. I am absolutely smitten with Fearrington for its gorgeous trails, shops, eateries and spa. If you decide extend your Pittsboro day trip to two day (which is easy to do!), I definitely recommend staying here. The experience is outstanding!  Check out more here, here, and here.
A Night at the Fearrington House Inn(Photo by Matt)

I hope you’re having a great Thursday! Be sure to check on Pittsboro if you’re in the area!  It’s definitely worth the trip!



2 thoughts on “15 Things to Do in Pittsboro, NC

  1. Shelby

    I LOVE this. Pittsboro is home <3 I moved there when I was in 8th grade and my first job ever was actually at Fearrington in a plant/flower shop! It doesn't exist anymore but I love visiting Fearrington every time I go back home to visit the fam!

    xo, Shelby

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