Four Perfect Date Nights in Pittsboro, NC

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Build your perfect Chatham County date night using these readers’ favorite recommendations

By Anna-Rhesa Versola | Photography by John Michael Simpson

Rest[aurant] & Relaxation

4PM – Spa at Bell House

Treat yourself and that special someone to a relaxing experience. Choose a massage, skin treatment or a seasonal manicure at Spa at Bell House on East Salisbury Street. Book concurrent sessions for 60 minutes of luxury.

6PM – The Beagle

Around the corner, find The Beagle behind a yellow door. Owners Leslie Cox and Brian Cox have crafted a welcoming dog-themed atmosphere that harmonizes with its equally creative menu, which features cocktails like “The English Bulldog” (rye, sherry, Aperol and orange) and “The Rescue” (gin, lime, egg white, basil-ginger shrub and ginger). Plus, on the first Wednesday of every month, 10% of the night’s proceeds benefit cats and dogs in need at Chatham Animal Rescue and Education.

8PM – Page Vernon Park

Walk off those delicious bites and sips beneath the lighted trees along Hillsboro Street up to Page Vernon Park and take in the cool evening air. Sit on the brick wall or find a picnic table and watch the stars emerge overhead.

Jennifer and Sydney sit at the bar smiling as they toast with their wine glasses to kick off date night.
Jennifer Larrimore and her wife, Sydney Decker, enjoy drinks before dinner at Postal Fish Company’s bar.

Young at Heart

4PM – S&T’s Soda Shoppe

Have dessert first at this Hillsboro Street standby. The old-school ice-cream shop and soda counter is a charming place to split a handspun milkshake with two straws, share a giant cone or dig into a banana split piled high with toppings.

6PM – The Mod

Order a wood-fired pizza at The Mod, located just south of the courthouse along Sanford Road. The menu offers both gluten-free and vegan options, perfect for those with dietary restrictions, plus a full menu of cocktails and beer on tap. Hang outside on the patio in nice weather to enjoy a conversation or some people-watching by the fire pit.

8PM – The Other Side

After your last slice, slide on over to The Other Side, The Mod’s sports bar and entertainment space next door for weekly live entertainment. Team up for trivia hosted by Chatham native Jon Spoon on Wednesdays, or play music bingo with DJ Ones on Thursdays. Or challenge your date to a round of pool, pingpong, foosball or cornhole. On weekends, there’s plenty of room to cut a rug on the dance floor.

Tails & Scales

5PM – Carolina Tiger Rescue

Book a twilight tour at Carolina Tiger Rescue (and book early, because they sell out fast!) These evening tours are held during special times on Fridays and Saturdays from April through October, and are designed for visitors to learn about and visit the animal sanctuary’s big cats at a time of day when they are most active – maybe you’ll be lucky enough to hear them roar in chorus at dusk.

7PM – Postal Fish Company

Head to Postal Fish Company on Salisbury Street for delicious seafood served up inside a renovated mid-century modern post office. Chef Bill Hartley ensures the restaurant’s rotating menu of dishes featuring fish and shellfish are hand selected from the most trusted fishermen in the South Atlantic; each meal is served with fresh takes on classic Southern accompaniments like grits, okra and sweet corn.

9PM – The City Tap

Make your way over to The City Tap after dinner to listen to a live band on Fridays and Saturdays. Grab a beer and a table outside on the covered patio and unwind as the night breeze fills with music. On the off chance you’re still hungry, try the loaded nachos, spinach artichoke dip or Mediterranean pita for a late-night snack.

A heaping portion of well-cooked catfish and red peas sits in a blue bowl, garnished and topped with relish. Two drinks and another dish (also in a bowl) are visible in the background, but out of focus.
Postal Fish Company’s blackened Pitt County catfish is served over a bed of stewed Sea Island red peas and chorizo and topped with a bright chow chow relish.

An Elegant Evening

4:30PM – Davenport’s Cafe Diem

A cabinet of curiosities awaits at Davenport’s Cafe Diem, a steampunk-themed coffee shop on Hillsboro Street. Cozy up with your date over a “Lovelace” (an Earl Grey tea mixed with hot chocolate) and take in the offbeat art and antiques that adorn the walls.

6PM – Pollinator Paradise Garden

Stroll by Chatham MillsPollinator Paradise Garden and its more than 225 species of perennials, trees, shrubs and grasses, 85% of which are native to North Carolina.

7PM – The Sycamore at Chatham Mills

After your walk through the garden, head to The Sycamore at Chatham Mills, where owners Maria Parker-Lewis and Greg Lewis created a fine-dining experience inside a restored textile mill. Executive chef Shane Ingram, who has years of experience working in Michelin-starred restaurants, serves elevated cuisine inspired by seasonal local ingredients. On Wednesday nights, live jazz takes over the lounge, while a piano player adds to the ambiance Thursdays through Saturdays.

A close-up of Sydney and Jennifer's hands as they scoop their spoons into the dessert.
Sydney and Jennifer dig into a slice of crumbly fig cake topped with honey-ginger ice cream for dessert at Postal Fish Company.

More Romantic Pittsboro Spots

  • Vino!! Wine Shop has reopened in a new and improved space at 89 Hillsboro Street, and offers regular wine tastings as well as pairing plates, perfect for sharing a relaxing evening with your special someone.
  • Craving something new and fresh? The West End eatery offers a rotating menu of breakfast, brunch and lunch plates using local ingredients. Open Wednesday through Sunday at 23 Rectory Street.
  • Creative Creamery is a family-owned ice cream shop dreaming up sundaes and milkshakes piled high with delightful flavors. Visit them daily at 216 E. 11th Street in Siler City.
  • If your date night looks more casual, stop in to Carolina Brewery for delicious pub fare (try the burgers!) and award-winning beer brewed on site.
  • Or, plan a shopping date to go treasure hunting at some of our readers’ favorite local stores!

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Anna-Rhesa Versola

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