Perfect Getaway to Southern Pines

By Charles McCool

Perfect Getaway to Southern Pines

Couples looking for a relaxing, romantic, and memorable vacation getaway should move Southern Pines, North Carolina to the top of their list. Nestled in the North Carolina Sandhills, the area was once a winter retreat for wealthy New Englanders but now is a sporty, foodie, and rejuvenating destination for everyone all year round. Southern Pines itself is a wonderfully walkable town. The train station is in the center of downtown Southern Pines and within a 10-minute walk of dozens of restaurants, shops, and attractions. Visitors arriving by train can enjoy a carefree and car-free vacation but Uber and Lyft rides are readily available to reach places outside the quaint downtown area.

Southern Pines Train Station

A super convenient Amtrak train departs Washington DC Union Station at 3 pm and arrives in Southern Pines at 10:30 pm. If you do drive to Southern Pines, you will be impressed with plentiful free parking areas.

Every first Friday evening from March through October a band plays at Sunrise Park next to the Sunrise Theatre. The surrounding downtown Southern Pines streets are closed to traffic and people can walk around with open containers. It is a fun time to visit.

Tanglewood B&B is on a working horse farm.

A phenomenal place for couples to stay in Southern Pines is Tanglewood Farm B&B. Located only three miles from downtown Southern Pines, Tanglewood is a 10-acre working farm with a dozen free-range chickens and several horses. Owner Lindsay O’Reilly is a trained chef and her weekend breakfast is a highlight of any stay. Three suites are lovingly decorated, fully stocked, and each has a patio area facing the farm – a splendid place for morning tea/coffee, happy hour drinks, or evening star gazing. Allow time to explore the 4,000-acre woodland Walthour-Moss Foundation across the street.

Another fantastic lodging option, The Jefferson Inn, is located just a short block from the Southern Pines train station. This completely modernized luxury historic property – the only boutique hotel in the Sandhills region – has 14 comfortable suites, luxurious bathrooms, a classic Southern porch with rocking chairs, and an intimate patio featuring live music most nights. The Jefferson Inn is within convenient walking distance to everything in downtown Southern Pines.

Honeycutt Jewelers located on a corner in Southern Pines NC

The North Carolina Sandhills area is known for a preponderance of pine trees but do not neglect to bask in the glory of the magnificent Southern magnolias. Plenty of both trees line the downtown Southern Pines streets and parks. One splendid specimen of each tree is right next to each other near the Southern Pines public library. The Story Walk around the public library is cute, featuring alternate fairy tales created by local children. Walking around downtown Southern Pines is a treat and you will make your own discoveries.

The 26-acre property surrounding the Weymouth Center for Arts & Humanities is a nice change from the downtown scene and is less than a 3/4 mile walk from the Southern Pines train station. Several garden areas offer ideal spots for a romantic picnic lunch and/or a bottle of wine! Avid readers will enjoy visiting the North Carolina Literary Hall of Fame on the second floor of the Weymouth Center. The adjacent Boyd Tract of Weymouth Woods Sandhills Nature Preserve includes an easy one-mile loop trail. Along that Round Timber trail, look for a hidden side path leading to the world’s oldest longleaf pine tree.

Other places hiking fans will enjoy getting their 10,000 plus daily steps include the Weymouth Woods Tract of the Weymouth Woods Sandhills Nature Preserve (over five miles of wooded trails) and Reservoir Park (two-mile loop trail around the lake).

SCC Horticultural Gardens

Visit the Sandhills Horticultural Garden to see a wide variety of trees including the largest collection of hollies on the US East coast. Several areas provide romantic settings for couples – including the boardwalk trail through the native wetland garden, Sir Walter Raleigh Garden, Japanese garden, conifer and woodland sections. Bask in an inspirational and relaxing setting with Adirondack chairs for two people or bring a picnic lunch and enjoy the Succulent Garden patio.

No visit to Southern Pines is complete without a spa treatment. Several day spas are in downtown Southern Pines but for a special splurge head to The Spa at Pinehurst Resort. After all that hiking, relax in their steam room and hot tub before and after your deep tissue massage. Reserve a horse carriage ride in advance and meet your driver and carriage in front of the Carolina Hotel entrance. Tour the historic Village of Pinehurst streets with the knowledgeable guide and return the waves from adoring fans at the outside cafes. Visit the Tufts Archives and explore Pinehurst history, or purchase the Historic Walking Tour of the Village of Pinehurst book and learn about the quaint homes strolling the streets designed long ago by Frederick Law Olmsted.

Learn more about our favorite places to eat and drink around the Sandhills.

DC based Charles McCool is recognized by Cision for having one of the Top US Travel Accounts on Twitter. Follow his journeys on and check out his wife Julie’s work at

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