Southern Pines has such a walkable downtown, and there are so many unique shops to browse. Monkee’s of the Pines has a delightful 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. Against the Grain Shoppe features over 75% of its inventory from small businesses right in Moore County. We also had to pop in The Country Bookshop to check out the newest releases and pick up some new reads. This bookshop has been around since 1953.

There are quite a few trails to pick from in Moore County, which is a great way to stretch your legs and catch up. One of my favorite trails at Southern Pines Reservoir Greenway. For more Moore County trails, check out this list.

The Village Wine Shop is the cutest spot in the Village of Pinehurst to grab a bottle of wine and snacks for your girls’ weekend. Grab a glass of wine or a coffee while you are there and enjoy cozying up in their elegant space or sitting on their sidewalk and enjoying the sunshine and a little people-watching. Moore County offers a Sandhills Wine Trail passport and this is one of the stops along the way if that is of interest to you as well.

While you are in the Village, be sure to pop by Teramasu to explore the beautiful handmade jewelry collection. This shop also boasts a one-of-a-kind collection of women’s clothing and accessories and home decor items.

Moore County has a fantastic selection of antique shops and it is such a fun way to spend a Saturday afternoon with your girlfriends. After grabbing a coffee at Buggy Town Coffee in Carthage, we shopped Eliza Quinn Creates and brought home so many home decor and candles. We scored great deals on some amazing vintage pieces at the Vintage Barn. We also enjoyed shopping Market 107 and picking up some unique snacks and more home decor items. We popped down to Cameron and really enjoyed exploring Old Hardware Vintage Depot and Junk n Java.

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.

Looking for something fun and unique to do while in town? Book tickets on the Sandhills Trolley Tour for one of their ticketed events! They have so many fun options, including murder mysteries, brunch haunted history tours, and brewery tours.

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.

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.

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.

Buggy Town Coffee in Carthage is the perfect spot for grabbing a coffee or a lavender lemonade before heading out to shop! Buggy Town Coffee offers a great selection of food options as well.

Elliott’s on Linden is located in Pinehurst and offers a delicious selection of cocktails and a farm fresh dining menu! We loved the scallops, served with caviar, tuna tartare, and the squid ink pasta. The interior of the restaurant is so bright and pretty, too.

Before heading out of town, we stopped by the Roast Office Coffee Shop for coffee and breakfast and it was such a fun experience! Located in the former post office, the Roast Office serves up excellent seasonal coffees and we loved the Southern Bagel. It’s served with black-eyed pea hummus, avocado, and greens on an everything bagel. While you’re waiting for your food, be sure to browse the used bookstore in the space as well.

Spending a day at the Pinehurst spa is such a wonderful way to unwind and relax. There are many amenities to enjoy in addition to your treatment including a sauna, hot tub, and pool. They also serve up delicious smoothies and offer food and beverage options as well. Book the Pinehurst massage and Pinehurst facial for a relaxing experience and plan to stay and lounge by the pool post-treatment.

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, comfortable, and welcoming. We booked two rooms with double beds and ample space for our girls’ weekend experience!

Meghan Grant is the creator and writer of the Triangle-based blog, I’m Fixin’ To. For more gems, follow @imfixintoblog on Facebook, Instagram, Twitter and visit I’m Fixin’ To.