Valentine’s Day in Chatham County

Pittsboro, NC – I’m always writing about the great outdoors in Chatham County, but I like getting dressed up as much as the next girl. Here’s a list of places in Chatham County that are spicing it up  for Valentine’s Day.

Oakleaf Restaurant

I wrote about Oakleaf back in November, but it’s just gotten a major push from resturant critic Greg Cox of the News & Observer. He named Oakleaf in Pittsboro as co-winner of  “Triangle Restaurant of the Year.” How about that!

From my November story:

Oakleaf, a new upscale restaurant housed in the historic Chatham Mill, is a progressive American restaurant with a focus on locally-sourced and sustainably raised/harvested ingredients.

Oakleaf features seafood from the Carolinas, locally-raised meats and poultry, and produce sourced primarily from our farmers in Chatham and surrounding counties. The restaurant strives for a sophisticated dining experience in a comfortable and inviting environment.

Make a reservation online.

480 Hillsboro St.
Pittsboro, NC 27312

Pittsboro Roadhouse

The Pittsboro Roadhouse is a relatively new eatery in Pittsboro. It opened in August 2012 in the space formerly occupied by the General Store Cafe. They are hosting a Valentine’s Day Dinner for Sweethearts that includes a special menu just for the night, including champagne and chocolate desserts. The menu includes a shared appetizer for two, house salad and your choice of 1 of 5 entrees, as well as a shared dessert sampler for two.

No reservations are necessary. Just come between 5 pm and 8:30 pm and our hostesses will seat you. Tell your waitress that you want the Valentine’s Day Dinner.

Pittsboro Roadhouse
35 West Street
Pittsboro, NC, 27312
(919) 542-2432

Wine & Cheese Soirée

The Abundance Foundation is hosting a Valentine’s Day Wine and Cheese Soirée!

Eat, drink and learn everything about pairing your two favorite guilty pleasures together! On this delicious Valentines’ Day evening workshop, you will engage your taste buds and savor the pairs they create.

You and your date will be introduced to cheese basics, exploring types, flavors, textures and history. Then the class will move through guidelines for pairing appropriate wines to delicious local cheeses, sampling our way through it all.

$75 per couple – Registration and Pre-payment required. You can register here. If you have any questions, you can call them at 919-533-5181 or email

Wine & Cheese Soirée
The Abundance Foundation
220 Lorax Lane #5
Pittsboro, NC 27312

Carolina Crossroads Restaurant

Just up the road from Pittsboro is Carolina Crossroads Restaurant at The Carolina Inn. They’ve created a special Valentines Day Dinner menu.

Per their website, “Enjoy an exceptional 4-course meal created by Executive Chef James Clark, share a romantic dessert by Pastry Chef Sara Thomas and celebrate with a champagne toast. Dinner includes a rose for your one and only to make the evening complete.” Sounds yummy.

$75 per person. Call for reservations at 919-918-2735.

Carolina Crossroads Restaurant
211 Pittsboro Street
Chapel Hill, NC 27516

Want to check out some other special Valentines Day menu’s available in the area? Visit Open Table for more listings.


Heart photo by Skyler817.

1 reply
  1. Bill Byrne
    Bill Byrne says:

    Hi Julie, how are you doing ? Enjoyed your e-mail ” Valentine’s Day ” recap of nice places to wine and dine with one’s Sweetheart. That would be nice to do if I was in Dining out shape, ha,ha. Still think about you.

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