Southern Pines NC is such a lovely, charming town located in Moore County. Keep reading for my weekend guide to the best things to do there! While Southern Pines was slow to develop because of the sandy soil, it quickly became an important spot as railroads developed in the 19th century. The historic district of Southern Pines is split with the still active railroad and offers delicious restaurants, fun breweries, quaint shops, and lots to do outdoors! It is quite a beautiful, short drive into town from Raleigh, past the horse farms and gorgeous homes.
Southern Pines is one of the best weekend getaway destinations whether you enjoy golf or are looking for a day trip to do some shopping or a relaxing weekend opportunity. Today, I am sharing a roundup of activities that you can do to make the best out of your weekend in Southern Pines NC.
This article was originally published in September 2021 and has since been updated and recirculated for February 2024.
What to do in Southern Pines, NC: Weekend Edition
What to Do in Southern Pines NC
Shop Local in Historic Downtown Southern Pines
Southern Pines has such a walkable downtown, and there are so many unique shops to browse. Monkee’s of the Pines has such a gorgeous selection of women’s fashion, jewelry, and accessories. R. Riveter specializes in hand-made bags from military uniforms, a business started by two military spouses. The shop also has a variety of gift items as well, such as R. Riveter candles. My personal favorite is audacious, with citrus and cedar notes. Against the Grain Shoppe features over 75% of its inventory from small businesses right in Moore County. I picked up a few gifts for the upcoming holiday season from this shop!
Pick Up a New Release at The Country Bookshop
Photos by GloryRoze Photography
I will always stop by an independent bookstore and The Country Bookshop has quite a bit to offer! Between their Southern Pines/Pinehurst picks, their new release options, and their gift ideas, it is such a great shop to spend time in. We found such great options
Have a Pint at Southern Pines Brewing Company
Check out Southern Pines Brewing Company on Pennsylvania Ave. The taproom offers gorgeous outdoor seating with views of downtown, heaters for cooler evenings, and food trucks. There are lots of options on tap, including wine, too. David enjoyed the Mexican Lager and he also likes the Man of Law.
Stretch your Legs on the Southern Pines Reservoir Greenway
This 2.1 mile loop is a great way to stretch your legs as you walk around the Southern Pines Reservoir. The 165-acre Reservoir Park is home to a 95-acre lake, a natural Disc-Golf course, a boat ramp with boat and kayak docks, and offers a free rod, reel, and tackle rental.
Interested in more trails? Check out Weymouth Woods Sandhills Nature Preserve. This is on my list of places to visit on our next trip to Southern Pines!
Check out the North Carolina Literary Hall of Fame at Weymouth Center for the Arts and Humanities
Photo via Weymouth Center Instagram
This fabulous venue is claimed to have started the Southern literary revival and hosted writers such as Thomas Wolfe and F. Scott Fitzgerald. The property was the first nature preserve in the North Carolina parks system. The Weymouth Center houses the North Carolina Literary Hall of Fame and the grounds are open daily. Tours of the magnificent Boyd House are offered during weekdays. Check out this page for more on the history of this gorgeous property and the Boyd family’s impact on Moore County.
Catch Live Music at First Friday
This monthly event runs May-November, taking a break in July, and is a fun community event to catch live music on the grassy knoll beside the Sunrise Theatre. There are food trucks, vendors, and Southern Pines beer available for purchase while listening to local bands.
Enjoy a Night Cap at 1901 Lounge
Photos by GloryRoze Photography
1901 Lounge recently opened on the first floor of the historic Jefferson Inn in downtown Southern Pines and offers a unique line-up of cocktails and a nice wine list. The space is absolutely stunning and the staff is incredibly kind and helpful. We really enjoyed our cocktails and learning how to play chess. It’s the perfect spot for a pre-dinner drink or a nightcap.
Where to Eat in Southern Pines NC
Grab a Coffee from Java Bean Roasting Co.
While you are out for a stroll downtown, stop and grab a cup of Joe from Java Bean. This coffee shop has lots of outdoor seating with great coffee and pastries. It is cash only so prepare accordingly.
Dine Al Fresco at the Sly Fox Pub
The Sly Fox offers a menu of elevated European and Indian Pub food with patio seating areas, including one area under a beautiful ivy-covered wall. We opted for burgers, and the Locavore and the Pub burgers are delicious options. I subbed my fries for the mac & cheese and would encourage you to make the same decision!
Try a Crepe at Betsy’s Crepes
Photos by GloryRoze Photography
This gem of a restaurant serves breakfast and lunch, featuring sweet and savory crepes, plus soups, paninis, and salads. Betsy’s also offers gluten-free crepe options. Don’t let the line deter you–it moves quickly. Don’t sleep on their breakfast sandwiches either.
Lunch at the Bell Tree Tavern
Bell Tree Tavern is a great, local spot to grab lunch and catch a game. Or, you might opt to enjoy the expansive, dog-friendly patio. The chicken quesadilla and chicken BLT wrap were fantastic! And peep that fried okra.
Enjoy a Farm to Table Meal at Scott’s Table
We enjoyed our experience at Scott’s Table, from the welcoming service to the entrees we ordered. Scott’s Table focuses on using quality, fresh ingredients and selects produce from local North Carolina sources. We started our meal with pimento cheese, which is served with crostini. David ordered the blackened chicken sandwich while I had the crab cake.
Dine at Ashten’s
Photos by GloryRoze Photography
Ashten’s is a restaurant staple in Southern Pines, having been open since 1997. Their bar offers an expansive drink selection, plus small bites. The interior concept is elegant, yet comfortable, inspired by an English manor. It also has outdoor seating, making it a perfect spot to do some people-watching.
We ordered the artichoke heart pops, ostrich koftas, and Rueben egg rolls to start. For entrees, we split the duck and the hoop cheese and mushroom burger. Whatever you do, order their double chocolate salted caramel cake for dessert. Their menu is so fun and the service every time I have been has been outstanding. Be sure to make a reservation ahead of time.
Where to Stay in Southern Pines NC
The Jefferson Inn
Photos by GloryRoze Photography
The Jefferson Inn & 1901 Lounge is a fourteen-room, 100+ year-old landmark Inn with a beautiful speakeasy specializing in craft cocktails, located in the heart of the Downtown Southern Pines Historic District. It is the perfect location for walking around downtown Southern Pines to explore and a short drive away to surrounding Moore County area towns! The inn went through a renovation in 2023 and is incredibly cozy and welcoming. We had a wonderful stay here and I look forward to a return trip! See more about the 1901 Lounge in the What to Do section!
For another Moore County favorite, check out this travel guide for Pinehurst here. Looking for other small towns for great weekend getaways? Check out Black Mountain or Blowing Rock!
Thank you to Pinehurst Southern Pines Aberdeen Area: Home of American Golf for partnering with I’m Fixin’ To. As always, all opinions on my experiences are my own.
Shop What I Packed for My Weekend in Southern Pines NC
