2015 Guide to Holiday Events in Chatham County

Christmas in Chatham County

The best part about the Holiday season is the time you’ll get to spend enjoying the company of friends and family. Don’t be a Scrooge this year and stay indoors — get out and meet your neighbors! Chatham County hosts some awesome, family-friendly events, and you’ll have the opportunity for fellowship every weekend through Christmas.

I’ve grouped this guide based on event category. If you know of another event you think should be included, don’t hesitate to email me!

Festivals and Parades:

Pittsboro Holly Days
Sunday, November 22 – Saturday, December 19
Pittsboro, NC

Pittsboro Holly Days is a month-long celebration of the holiday season, including everything from arts and crafts to tree-lighting to a parade in downtown Pittsboro. For a full schedule of times, directions and details, visit the Town of Pittsboro’s website here.

Siler City Christmas Parade
Thursday, December 3, 7:00 p.m.
Downtown Siler City, NC

Join other Chatham residents for the Siler City Christmas Parade. This is always a favorite event for locals and people in surrounding counties. This year’s parade theme is “The Birth of Christmas.” In the courtyard on Chatham Avenue, the “Hangout Worship Band” will perform live onstage, before and after the parade. Also, the Siler City Merchant’s Association will have their annual Tree Lighting at 6:30 p.m., and Santa will visit with children in the courtyard right after the parade.

The parade will follow the usual route – down S. Chatham, right onto Beaver Street to S. Birch Street, left onto W. Raleigh Street to Park Shopping Center (Maxway) and will disperse from here.

Pittsboro Christmas Parade
Sunday, December 13, 3 p.m.
Downtown Pittsboro, NC

This has long been one of my favorite holiday events. Hosted by the Town of Pittsboro, the Pittsboro Christmas Parade includes marching bands, dancers, holiday revelers, and Santa Claus marching through downtown. The parade route starts at the Food Lion Shopping Center and travels west down Hwy 64 past the courthouse. The Town of Pittsboro has a map of the exact route. Because it’s centrally-located, it will make for easy access, regardless of where you live.

Christmas in Chatham County


Charlie Lovett – The Further Adventures of Ebenezer Scrooge
Tuesday, December 14, 2:00 p.m.
McIntyre’s Books, 2000 Fearrington Village Center, Pittsboro, NC 27312

Listen to a delightful sequel to Dickens’s beloved A Christmas Carol by the bestselling author of First Impressions and The Bookman’s Tale. Written in uncannily Dickensian prose, Charlie Lovett’s, The Further Adventures of Ebenezer Scrooge is both a loving and winking tribute to the Victorian classic, perfect for readers of A Christmas Carol and other timeless holiday tales.

A Christmas Carol Dinner Show
Saturday, Sunday, December 15, 16, 22, 23
39 West Street, Downtown Pittsboro, NC

Celebrate the Holidays at the Pittsboro Roadhouse with the premiere of A Christmas Carol Dinner Show produced by the Phoenix Theater Company. Please call (919) 542.2432 to be on the waitlist.

Miracle on Hillsboro Street
Saturday, December 19, 2 p.m. – 3:30 p.m.
Chatham County Courthouse, Pittsboro, NC

A high-profile trial is taking place this year at the Chatham County Courthouse, and the defendant is … Santa Claus!! A county judge will preside over the trial with real lawyers, local actors and the real Kris Kringle. Come root for a Miracle on Hillsboro Street!

Tree Lighting Celebrations:

Pittsboro Tree Lighting Celebration
Sunday, November 22, 5 p.m. – 7 p.m.
Chatham County Courthouse, Pittsboro, NC

To kick off Pittsboro Holly Days, Hillsboro Street will make way for an old-fashioned Christmas celebration featuring school choirs, carolers, Santa Al, hot cocoa, shopping, and more. The festivities will culminate with the lighting of a 15-foot Christmas tree at the Courthouse. Pittsboro businesses are planning to host special events all day.

Siler City Tree Lighting
Thursday, December 3, 6:30 p.m.
Downtown Siler City, NC

Right before the Siler City Christmas Parade, the Siler CIty Merchant’s Association will host the annual Tree Lighting in the courtyard on Chatham Avenue.


Chatham County GIVING PARTY – Ladies Night of Giving
Tuesday, December 1, 7:00 p.m. – 9:00 p.m.
Briar Chapel Clubhouse, Chapel Hill, NC

Come learn about and support five outstanding Chatham County Nonprofits doing important work right here in our backyard. Hosted by Chatham Connecting, the goal is to raise $5,000. If 100 ladies donated $50 each, the non-profit organization could easily meet this goal and provide tremendous support to the Chatham community. Grab a girl friend, grab your checkbook and head on over for an evening of mingling, drinks, girl time, and most importantly, the opportunity to Give Until It Feels Good! Click here for the evite and additional information.

Pittsboro Roadhouse Community Christmas Party
Sunday, December 7, 10 a.m. Volunteer Lunch Packing; 3:30 p.m. Party
39 West Street, Downtown Pittsboro, NC

Every year on the day of the annual Town Christmas Parade the Pittsboro Roadhouse hosts a community Christmas Party in Pittsboro, right after the parade. Kids can meet with Santa Claus and enjoy crafts, while you sit back and enjoy the refreshments, Christmas cookies, Christmas trees, and great holiday cheer to share with all.

Arrive early at 10 a.m. for a volunteer lunch packing, followed by brunch at 10:30!


Santa’s Secret Menu
Available November 19 – December 27
Carolina Brewery & Grill, 120 Lowes Dr, Ste 100 Pittsboro, NC

Carolina Brewery & Grill, a local favorite, offers weekly tours every Saturday, year-round, 2 p.m. – 3 p.m. During the Holiday season, you can  enjoy a secret Santa menu of Truffle Fries, Fried Chicken Sliders, and a special Santa’s Secret Holiday Ale!

Fall Harvest Wine Dinner
Saturday, November 21, 7 p.m.
Vino!!! Wine Shop, 89 Hillsboro St, Suite D Pittsboro, NC

Vino!! Wine Shop specializes in selling high quality and unique wine and beer from around the world. Enjoy a fantastic four-course meal at 458 West B&B. For a full menu, click here.

Price is $60 per person, not including tax and gratuity, and 17 seats available. Please call (919) 491.4229 for reservations. After dinner, stay the night and receive a 20 percent discount on your room.

Third Annual Gingerbread Decorating Workshop
Monday, December 20, 2 p.m. – 4 p.m.
480 Hillsboro St, Pittsboro, NC

Gumdrops, Candy Canes, and Peppermints! Oakleaf is converted to a candy shop for the afternoon so that you and yours can decorate gingerbread houses. Enjoy hot chocolate, coffee, and cookies while you create your masterpiece. The price is $35 per house, with a maximum of four guests per house. Reservations are required, so go ahead and reserve your spot by clicking here.

Shopping Events/Arts & Crafts:

Christmas Tree Market
Thursday – Sunday, 9 a.m. until dark
Phillips Farm of Chatham, 1282 Hanks Chapel Road, Pittsboro, NC

Be sure you get your Christmas tree to decorate! Phillips Farm’s pre-cut Fraser Fir and White Pine Christmas trees are grown in Alleghany County, North Carolina. With trees of every size available, from small three-foot tabletops to large 13-foot beauties, whatever your size need, these guys can fill it.

The farm also offers Choose & Cut trees, which are grown in Chatham County. Please call (919) 427.4738 for any question regarding Choose & Cut.  

Holiday Furniture Open House
Sunday, November 22, Noon – 7 p.m.
Reclamation Home Furnishings and Company, 102 Hillsboro St Pittsboro, NC

Serving homemade hot apple cider and cookies and donating 10 percent of sales to the Family Violence and Rape Crisis Center of Chatham County, the RHF and Company Holiday Open House is a great opportunity to “shop for a cause.”

Small Business Saturday
November 28, All Day
Downtown Pittsboro, NC

Come out and support the family-owned small businesses in downtown Pittsboro on the last Saturday of November. Small Business Saturday will be a great way to cap your week of celebration — especially after hours of fighting on Black Friday! There are plenty of events happening (get the full schedule here) that will get you in a Holiday mood!

Starrlight Mead Holiday Decorating
November 29, 1:00 p.m. – 5:00 p.m.
480 Hillsboro Street, Suite 1000, Pittsboro, NC

Starrlight Mead, Pittsboro’s own meadery, is open from noon to 6 p.m. on Small Business Saturday. Pick up unique gifts for your special friends and family or just relax with a glass of mead. The next day, Starrlight Mead’s favorite fairies will be out to help with your personal holiday decorating. Fairy Hair Flare will be sparkling you up for the holidays. Please call (919) 533.6314 for an appointment.

Holiday Kiln Opening
Saturday – Sunday, December 5, 6, 12, 13, 10 a.m. – 5 p.m.
2555 George York Road, Randleman, NC 27317

Some fantastic pots were made by Joseph and Curry this cycle at Joseph Sand Pottery. With the 15th firing of the large kiln, the pottery has arrived at five years of production. Get a unique gift for a family member by heading out to the Holiday Kiln Opening. Get a preview of these beautiful works of art by checking out the gallery here.

First Sunday Artisan Fair
Sunday, December 6, Noon – 5 p.m.
Downtown Pittsboro, NC

A week after Small Business Saturday, head to the Historical Museum in downtown Pittsboro for  an artisan market featuring handmade crafts, music, and food. For a full list of vendors participating, click here.

Fearrington Bird Walk
Saturday, December 12 , 7:30 a.m. – 9:30 a.m.
The Goat at Fearrington Village, 2000 Fearrington Village Center, Pittsboro, NC 27312

Join Mark Kosiewski, Conservation Chair for the New Hope Audubon Society, on a bird walk to enjoy the crisp December air. Mark will be pointing out Chatham County’s resident species, as well as our newly arrived winter birds. Meet at The Goat, and bring binoculars, a bottle of water, and your walking shoes. The group will explore Camden Park as well as the Bynum Bridge area.

Wine Tastings:

Blind Tasting Class: Red Wine
Thursday, December 3,  6:00 p.m.
The Fearrington Granary, 2000 Fearrington Village Center, Pittsboro, NC 27312

Join Wine Director Maximilian Kast to learn about analyzing wine without any preconceived notions of what is in the glass. At the class, you will taste six red wines blind, and talk about the methods of looking at the wines quality, how it was made, where it comes from, and why the wine in your glass tastes the way does. The tasting costs $35 dollars per person, including wine, cheese plate, service fee and tax. To reserve a spot, please call (919) 542.2121.

First Friday Wine Tasting
Friday, December 4, 6 p.m. – 9:30 p.m.
237 Center Grove Church Rd, Moncure, NC 27559

unWINEd is a wine store selling North Carolina wines by the bottle or by the glass in a country setting in Chatham County. Visit the cozy historic building with surrounding outdoor patios, and enjoy Bella Donna’s grilled pizza first Friday of each month.

*Gift idea! Cackalacky spice sauce and sweet sauce minis are available at unWINEd, making great stocking stuffers or small gifts for office friends. The winery also sells wine baskets and has staff on hand to help you select the right wines and products for your baskets.

Christmas in Chatham County

Did I Miss Anything?

If you know of another event you think should be included, don’t hesitate to email me!

Photos sourced from Flikr.