Pittsboro-Siler City Convention & Visitors Bureau

Pittsboro Tree Lighting Celebration
2025-11-23 15:00 - 17:00 (America/New_York) | Pittsboro, Pittsboro, NC, 27312, United States
Save the date for the Pittsboro Tree Lighting Celebration on Sun, Nov 23, 3pm-5pm. You’re invited to a fun-filled afternoon and evening that the whole family will enjoy. There will be a festive vendor market, perfect for holiday shopping, as well as live entertainment on the main stage, a visit from Santa Claus, a train ride and bounce house for the kids, delicious eats from local food trucks, and of course, a magical tree lighting ceremony.
Bring your friends, family, and holiday spirit as the Pittsboro community kicks off the season together with joy, laughter, and community cheer. Vendors are welcome to apply using this link.
For more information, contact Pittsboro Parks & Recreation at 984.282.6927.
See more downtown Pittsboro events.

4th Annual Thanksgiving Dinner with Quiltmaker Cafe
2025-11-27 12:00 - 16:00 | Quiltmaker Cafe, 75 W Salisbury St, Pittsboro, NC, 27312, United States
Join your community members and Quiltmaker Cafe for their 4th Annual Thanksgiving Dinner on Thu, Nov 27, 12pm-4pm. This is a ‘donate-what-you-can’ meal provided by local community chefs and restaurants, including 39 West Catering, West End & Kitchen and Catering, Ta Contento, and more! This year, they will offer dinner buffet-style at Quiltmaker’s future location (previously Postal Fish Company). Vegetarian and vegan options will be available. No registration required.

Holiday Bazaar at Bynum Front Porch
2025-11-29 10:00 - 14:00 | Bynum General Store, 950 Bynum Rd, Bynum, NC, 27228, United States
Get ready for the annual Holiday Bazaar at Bynum Front Porch on Sat, Nov 29, 10am-2pm. The Saturday after Thanksgiving, Bynum wakes up with a sparkle in the air. Down by the old general store, the front porch is strung with garland and twinkle lights, and the smell of Bynum’s famous chicken cracker stew drifts out to meet the crowd.
It’s Holiday Bazaar day, and the place hums like a hive. Inside, tables are stacked with local treasures — hand-thrown pottery still warm from the kiln, jewel-toned scarves, hand-poured soaps wrapped in brown paper, and framed photographs that catch the Haw River in every season. Paintings lean in little clusters, each one carrying the signature of a neighbor you’ve probably shared a laugh with. Shoppers drift from table to table, warm cider in one hand, gift list in the other.
Outside, the Bynum Front Porch Pickers are in full swing. Banjo, fiddle, guitar — the music rolls out over the lawn, spilling into the street where folks line up for hot stew, talking and laughing in puffs of white breath.
And just steps from the front porch, another tradition is in full gear — Christmas tree pickup. Trucks and SUVs pull in and out, loading up fresh-cut pines that will soon stand in living rooms all over Chatham County. You can smell them even from the porch, sharp and green, blending with the scent of stew and cider until the whole town smells like the holidays.
See more Bynum Front Porch events.

Siler City Christmas Parade
2025-12-04 19:00 - 21:00 | Historic Downtown Siler City, Siler City, NC, 27344, United States
Christmas is coming to Chatham County! Get ready to celebrate the holiday season with the Annual Siler City Christmas Parade on Thu, Dec 4, 7pm-9pm, proudly presented by the Chatham Chamber of Commerce, the Western Chatham Area Chamber, the Town of Siler City, and the Chatham News & Record. This year’s theme, “Songs of the Season”, will have you humming along as the floats roll by. Bring the whole family to enjoy the magic of the season at one of Siler City’s most beloved traditions. Festive floats, marching bands, local groups, and holiday lights will fill the streets of downtown Siler City with cheer. Don’t miss the grand finale as Santa Claus himself lights the Siler City Christmas Tree, officially ushering in the holiday spirit!
Organizers are currently accepting participant entries now for just $20 per unit. This event is free and open to the public, and complimentary photos with Santa will be available after the parade. For more information, please reach out to Cheryl Littleton at Cheryll@ChathamChamberNC.org or by phone at 984.265.9172.
See more Town of Siler City events.

Shakori 40 Ultra
2025-12-05 - 2025-12-06 | Shakori Hills, 1439 Henderson Tanyard Rd, Pittsboro, NC, 27312, United States
Shakori 40 Ultra on Fri, Dec 5-Sat, Dec 6, 2025, at the Shakori Hills Community Arts Center brings the running community together to race within nature and enjoy each other. They offer a 40-mile ultramarathon, a 40K open race for men and women, and a 40-mile age-graded team relay for up to 10 members—factoring in age and gender to determine the overall winning team. There’s also a 4-mile open race. You’ll have a blast at the Shakori 40, thanks to great camaraderie, live music, delicious food, camping, bonfires, craft beer, and so much more.
SCHEDULE
FRIDAY

1pm: Camping check-in.
2pm-8pm: Packet pickup at the Shakori Hills Barn.
6pm: Live music begins.
6:30pm: Jambalaya and chowder cookout.
10pm: Quiet time.

SATURDAY

5am: Venue opens.
6am: Packet pickup begins.
6:45am: 40-mile and 40K Individual Race meeting at the start line.
7am: 40-mile Individual Start.
7:10am: 40K Individual Start.
7:45am: Relay Race Meeting at the start line.
8am: Relay start.
10am: 4-mile Individual Start.
1pm: Relay awards.
2pm: 40K awards.
3pm: 40-mile awards.
5pm: All runners must be on the final lap.

See more Chatham Sports Alliance events.

Chatham Artists Guild Studio Tour
2025-12-06 10:00 - 17:00, 2025-12-07 12:00 - 17:00, 2025-12-13 08:00 - 17:00, 2025-12-14 12:00 - 17:00 | Chatham County, Chatham County, NC, United States
Experience fine arts, fine crafts, and open studios throughout Chatham County during the 2025 Chatham Artists Guild Studio Tour Sat, Dec 6 and 13, 10am-5pm, and Sun, Dec 7 and 14, 12pm-5pm. For the 33rd year, the Chatham Artists Guild proudly presents this rare opportunity to connect with local artists in an intimate setting – unlike any gallery or museum!
Take a relaxing drive through Chatham County’s rolling hills and pastoral farmlands to visit 59 talented artists in 41 studios that dot the countryside, with both private studios and visitor businesses participating. Meet the artists, learn about their process and artistic vision, and browse affordable original works of art. Grab a bite to eat in town, pack a picnic for your road trip, or skip the drive home and stay in one of our accommodations.
The Chatham Artists Guild Studio Tour is FREE and self-guided. It features artwork in all mediums at various prices, so there’s something for everyone!
FREQUENTLY ASKED QUESTIONS
Where can I find a tour brochure?
An interactive online brochure, with linked Google addresses for each stop, can be found here. Print brochures are also available at The Plant, NC Arts Incubator, Pittsboro Gallery of Arts, 79° West Innovation Hub at MOSAIC at Chatham Park, and several other Chatham County visitor businesses.
Who is featured on the tour?
The tour includes 39 stops featuring works from 54 local artists. Studios are scattered throughout Chatham County, including Pittsboro, Fearrington Village, Bynum, Chapel Hill (Chatham County), Sanford (Chatham County), and Apex (Chatham County). In addition to the private studios, tour exhibits are on display at Chatham Mills (student art) and Smelt Art Gallery at The Plant.
What can I do while I’m in Chatham County? Is there somewhere to eat? To stay?
Along the way, you’ll discover delicious food and drink, eclectic shops, and charming accommodations. Pair local food and art with a seasonal meal from one of our numerous farm-to-fork eateries. Restaurants along the tour route include Kingston 99 Kitchen and JDub’s PoBoys at The Plant, as well as Chatham Marketplace and The Sycamore at Chatham Mills. Fearrington Village is home to several studios and plenty to experience – Fearrington House Restaurant, McIntyre’s Books, and The Spa at Fearringon Village, just to name a few.
It’s easy to make a weekend of the tour by staying at the new Hampton Inn & Suites by Hilton Pittsboro, the luxurious Fearrington House Inn, or one of our cozy bed and breakfast inns, such as 458 West B&B, The Inn at Celebrity Dairy, or Jordan Lake B&B.
Are the studios accessible?
Most studios are accessible, meaning they have wheelchair-accessible entrances and parking. If you have accessibility concerns about specific studios, please email chathamartists@gmail.com or contact us.
I’ve found the perfect piece… but I don’t have room in my suitcase! Do the studios offer shipping?”
We welcome you to check with individual studios about their shipping policies, and most artists are likely willing to do so if asked.
Are the studios pet-friendly?
Since these are private studios, often located at an artist’s home, we kindly request that you leave your furry friends at home for this adventure. Service animals are welcome in compliance with Title III ADA Requirements for Service Animals.

Apple Brandy Opening Day
2025-12-07 12:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join Fair Game Beverage Company for their 2nd Annual Apple Brandy Opening Day on Sun, Dec 7, 12pm-6pm. There will be a holiday market, festive food, apple cider, Apple Brandy, a cocktail-making class, live music, and a cocktail competition! To enter the cocktail competition, email lisa@theplantnc.com.
This event is free and will take place both indoors and outdoors. The Plant is accessible to guests and will do its best to accommodate any additional requests—contact music@theplantnc.com with any accommodation requests or accessibility concerns. There is free parking. Pets are allowed but discouraged. This event is free. See all events at The Plant.

Siler City Christmas Market
2025-12-07 13:00 - 17:30 | Historic Downtown Siler City, Siler City, NC, 27344, United States
Celebrate the season with an afternoon full of holiday shopping, festive music, delicious food, and family fun at the second annual Siler City Christmas Market on Sun, Dec 7, 1pm-5:30pm. Stroll through downtown Siler City and discover unique gifts from local vendors, enjoy your favorite seasonal treats, and soak in the cheerful sounds of the Holiday Season. It’s the perfect way to experience small-town charm, support local businesses, and make merry memories with friends and families.
See more Town of Siler City events.

4th Annual Chili Cook Off
2025-12-07 17:00 - 20:00 | 580 Craft Beer, 354 East St, Pittsboro, NC, 27312, United States
Don’t miss 580’s Craft Beer’s 4th Annual Chili Cook Off on Sun, Dec 7, 5pm-8pm. Entry is free! Bring your favorite chili recipe to compete for a good cause – proceeds benefit the Mike Williams Scholarship Foundation. They contributed $1,00 in grants to students in Chatham County last year. Donations will also be accepted. Prizes will be available in the following categories:

Best chili.
Most interesting.
Best vegetarian.

The cookoff starts at 5:30pm. Free parking is available in front of the store. 580 Craft Beer is part of the Chatham County Craft Beverages & Country Inns Trail.

Holiday in the Park
2025-12-12 17:00 - 20:00 | Northwest District Park, 2413 Woody Store Road, Siler City, NC, 27344
Join Chatham County Parks, Recreation, and Cultural Resources for their annual Holiday in the Park on Fri, Dec 12, 5pm-8pm at Northwest District Park. This free, indoor and outdoor event will include pictures with Santa, a hayride, holiday-themed games and crafts, candy canes, warm drinks, carolers, and letters to Santa. The tree lighting at 5:15pm will kick off the event.
Continuing this year: a holiday market! If you are interested in being a holiday market vendor, email leigh.babcock@chathamcountync.gov.
This event is held indoors and outdoors at Northwest District Park by Chatham County Parks, Recreation, and Cultural Resources (CCPRCR). This event is free. All ages are welcome. See more CCPRCR events.

Bobby Gales and New Direction Bluegrass - Coming Home For Christmas
2025-12-12 18:00 - 21:00 | Bynum General Store, 950 Bynum Rd, Bynum, NC, 27228, United States
Join Bynum Front Porch for Bobby Gales and New Direction Bluegrass: Coming Home for Christmas on Fri, Dec 12, 6pm-9pm. Every December, the little town of Bynum fills with music, laughter, and the warmth of old friends gathering together. This year is no different—Bobby Gales is bringing his New Direction Bluegrass Band back home for a special Christmas concert at the historic Bynum General Store.
But don’t just come for the music—come hungry! Before the concert, they’ll be holding a community chili cookoff and potluck supper. Everyone is welcome at the table—no need to bring anything (though extra dishes are always appreciated, and vegetarian options are always part of the spread). It’s the kind of meal where you pass bowls and swap stories, where neighbors turn into family.
After supper, the music begins at 7pm. New Direction will fill the old store with bluegrass harmonies, Christmas songs, and the kind of joy that makes you feel rooted and lifted all at once. There’s no charge for admission or parking—just come as you are. A pith helmet will be passed for donations, as always. Easy and free parking is available at the Bynum ball field or in the lot beside the store.
See more Bynum Front Porch events.

Reindeer Run 5K
2025-12-13 08:00 - 11:00 | CCCC, 764 West St, Pittsboro, NC, 27312, United States
Join Chatham Partnership for Children at Central Carolina Community College for their annual Reindeer Run 5K on Sat, Dec 13, 8am-11am. Their USATF-certified course will start at CCCC and head towards downtown Pittsboro, then loop back for a finish at the campus. The 5K will start at 8am for all runners, with Race Day registration concluding at 7:45am. Please arrive early to pick up your race bib and find a parking spot.
Awards will be given for the following categories:

Individual overall.
Individual age groups.
Teams.

Race Day registration for the Reindeer Run 5K is limited to individual runners and Fun Run participants. Shirts will most likely not be available for these registrants.
Get ready for big smiles and little feet flying—Rudolph’s Fun Run is back! This joyful mini-race is perfect for our youngest runners, taking place entirely on the CCCC campus with an easy, fun ¾-mile course. The race kicks off at 9:10am, and every child who crosses the finish line will be greeted by Rudolph and friends with a medal. When you register, you’ll also have the option to order a race t-shirt. There is no need to attend packet pickup events for this one, unless you want to receive the t-shirt before the race; all other Fun Run items will be handed out on race day. It’s a festive, feel-good way to get kids moving and make unforgettable memories!
If you have any questions or concerns, please do not hesitate to contact Jazmin Mendoza Sosa, Communications and Development Coordinator, at jazmin@chathamkids.org. See more Chatham Sports Alliance events.

Christmas in Bennett
2025-12-13 11:00 - 19:00 | Bennett, Main Street , Bennett, NC, 27208, United States
Join Tri-County Ruritan Club for Christmas in Bennett on Sat, Dec 13, 11am-7pm. The day will feature cookies with Santa, local craft vendors, Christmas carolers, s’mores, a kiddie tractor pull, and the Christmas parade at 4pm. BBQ, pintos, and Chicken-N-Dumplings plates will be offered (dine-in and to-go). Lighting of the town Christmas Tree will follow the parade. More events in Bennett.

2025 Clayworxs Studios Show
2025-12-13 17:00 - 20:00 | Clayworx Studios, 136 Fayetteville St., Suite G, Pittsboro, 27312, United States
This is the event of the season that you don’t want to miss! The 4th Annual Clayworxs Studios Show is happening Sat, Dec 13, 5pm-8pm. Join them for an “Enchanting Evening” event to showcase and celebrate all of the fantastic art crafted at ClayWorx Studios during 2025. Clayworx will transform its studio into an elegant art gallery space for the evening, welcoming everyone to exhibit their work and enjoy the creations. This will be a very special event with great food and beverages, conversations, music, and a time to celebrate all things clay! Please invite your friends and family to the free festivities.
This event is free and takes place indoors. Clayworx Studios is located just off the circle in downtown Pittsboro, in the colorful building across from the fire station. Entry and free parking are available behind the building.

Pittsboro Christmas Parade
2025-12-14 15:00 - 17:00 | Pittsboro, Pittsboro, NC, 27312, United States
An annual tradition returns to downtown with the Pittsboro Christmas Parade on Sun, Dec 14, 3pm-5pm. There will be beautifully decorated floats built by local groups and businesses, filled to the brim with cheer and festive spirit, with fun costumes, floats, twinkling lights, and more. Seating will not be provided. Spectators are encouraged to bring their own chairs and blankets.
Registration to participate in the parade is now open. Click to register your group today! Floats will line up on Martin Luther King Drive at 1pm, and all others must be in place by 1:45pm for a prompt 3pm start to the parade. Information on road closures will be available soon. For more information, contact Pittsboro Parks & Recreation at 984.282.6927.
See more downtown Pittsboro events.

Holiday Dinner at The Sycamore
2025-12-16 17:00 - 20:30, 2025-12-17 17:00 - 20:30, 2025-12-18 17:00 - 20:30, 2025-12-19 17:00 - 20:30, 2025-12-20 17:00 - 20:30 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Join The Sycamore at Chatham Mills for a Holiday Dinner hosted throughout the week of Tue, Dec 16, 5pm-8:30pm. Celebrate the season in style at The Sycamore’s Holiday Dinner! Indulge in a festive Chef’s Tasting Menu ($85 per person), enjoy live holiday jazz, and make memories that sparkle. Seatings will be hosted on the following dates, with seatings available until 8:30pm:

Tue, Dec 16, 5pm-8:30pm.
Wed, Dec 17, 5pm-8:30pm.
Thu, Dec 18, 5pm-8:30pm.
Fri, Dec 19, 5pm-8:30pm.

Reservations are filling quickly — secure your table now. The menu for the evening is listed on The Sycamore’s website – click here for more details. The restaurant is ADA-compliant. Free parking is available in front of the restaurant. No pets allowed. See more events at Chatham Mills.

Jingle and Mingle with Chatham Pride Alliance
2025-12-18 18:00 - 21:00 | Thirsty Skull Brewing – Pittsboro, 684 West Street, Pittsboro, NC, 27312, United States
Join Chatham Pride Alliance for their second annual Jingle and Mingle on Thu, Dec 18, 6pm-9pm at Thirsty Skull Brewing – Pittsboro. Get ready for a festive evening of community, connection, and cheer! This gathering is more than a party – it’s a space to unwind, support one another, and strengthen the ties that make our community shine. Whether you’re reconnecting with familiar faces or meeting new friends, come as you are and share in the spirit of inclusion and joy that defines Chatham Pride.
This holiday season, Chatham Pride is hosting a silent auction alongside its Holiday Jingle & Mingle celebration! This auction features an array of exciting items and experiences donated by generous community partners, including Davenport’s Cafe Diem, 79 Degrees West, and Pittsboro Toys. There’s something for everyone on your holiday wish list!
This online auction will be open until Fri, Dec 20, giving you plenty of time to bid on your favorites. Not only does this add a bit of festive fun, but your participation directly supports Chatham Pride’s mission to create an inclusive, affirming space for all in Chatham County. By bidding, you’re not just taking home a special gift—you’re helping them build connections and provide support for loved ones during a season that’s all about togetherness. So, let’s raise our paddles (or click your submit buttons!) and spread some joy this holiday season.
This event is free and takes place indoors and outdoors, weather permitting. Thirsty Skull Brewing-Pittsboro is wheelchair-accessible. Free parking is available on-site. See more events at Thirsty Skull PBO. Part of the Chatham County Craft Beverages & Country Inns Trail.

Donald Davis Annual Storytelling
2025-12-20 11:00 - 12:00, 2025-12-21 14:00 - 15:00 | Fearrington Barn, 500 Market Street, Pittsboro, NC, 27312, United States
Fearrington Village is delighted to welcome back their beloved friend and storyteller, Donald Davis, for their Annual Storytelling on Sat, Dec 20, 11am-12pm and Sun, Dec 21, 2pm-3pm. After a hiatus last year, their fundraiser for the Chatham food pantry, CORA, is back. And they will tell you, the holidays just don’t start at McIntyre’s until Donald arrives in Fearrington. Please bring canned goods and/or a monetary donation to support our Chatham food pantry. Purchase your tickets here.
Capacity for this event is extremely limited – they expect to sell out rapidly. A $10 ticket is required to attend. Children cannot get in for free due to limited space. Unlike Fearrington’s other events, the ticket price is not deductible from related Event Books and Tapes. All monies gathered from tickets will go directly to CORA. The most needed items for this month are cereal, oatmeal packets, cooking oil, soup, apples, and pasta sauce. Find more information about CORA’s needs and programs here.
See more events at Fearrington Village. Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail.

Annual Dueling Sommelier Dinner
2025-12-21 17:45 - 20:45 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
‘Tis the season for the Annual Dueling Sommelier Wine Dinner with Vino!! Wine Shop on Sun, Dec 21, 5:45pm-8:45pm. Newcomer Sommelier Michael Maller of Orsini Wines is ready to take on former winner Annabel Butler, Level I Sommelier, of Oxford Street Merchants.
Chef Regan Stachler has crafted a fantastic four-course meal, which has been shared with both sommeliers. Each sommelier will then choose wines they believe best complement each course. Their selections WILL NOT be disclosed to each other OR anyone else until the night of the dinner! At the dinner, you will be served two glasses of wine (2-ounce pours each) with each course, which the sommeliers will describe in depth, WITHOUT telling you the varietal or the wine’s origin! Then, at the end of the evening, you will vote on which sommelier’s picks paired best with the meal to crown the winner. It is at this time that you, as well as the sommeliers, will finally find out what wines were selected for the meal. Who will win this duel of wines? You’ll decide! Get ready for one fabulous night of two battling sommeliers, four courses, and eight wines!
There are only 30 spots available at $160 per person, which includes tax and gratuity. Hurry up and make your reservations ASAP by calling 919.704.8612 or emailing anna@vinowineshopnc.com. Credit card information must be provided to hold the reservation. No refunds or cancellations are available after Thu, Dec 18.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

New Year's Eve Dinner at The Sycamore
2025-12-31 17:00 - 20:30 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Join The Sycamore at Chatham Mills for a New Year’s Eve Dinner on Wed, Dec 31, 5pm-8:30pm. They won’t be ringing in the new year, but they will have a beautifully curated Chef’s Tasting Menu ($110 per person, including one glass of champagne) designed to elevate your last evening of the year with rich flavors, seasonal inspiration, and elegant ambiance. With seatings available until 8:30pm, it’s the perfect way to savor a memorable, relaxed, and delicious final night of 2025. Reservations are filling quickly — secure your table now.
The menu for the evening is listed on The Sycamore’s website – click here for more details. The restaurant is ADA-compliant. Free parking is available in front of the restaurant. No pets allowed. See more events at Chatham Mills.

A Roving New Year's Eve!
2025-12-31 18:00 - 2026-01-01 00:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Welcome 2026 with A Roving New Year’s Eve at The Plant, Wed, Dec 31, 6pm-Thu, Jan 1, 12am. Join The Plant on New Year’s Eve for “one last crawl” to end 2025! Fair Game Beverage Company, bmc brewing, Starrlight Mead, and Koshu Sake will have festive beverages and creative spirit cocktails, specials, and, of course, sparkling wine by the bottle and glass. Kingston 99 Kitchen and Ta Contento will be open for dinner. There will be fire pits, an intention table, a dance party under the disco ball, and an hourly Apple Drop starting at 8pm and continuing until midnight to ring in 2026. Bring your friends and family- they’ve got something for everyone!
There is no cover fee for this free public event, and parking is free. Private tables and bottle service are available for a fee. Dress code is casual attire. The event takes place indoors and outdoors at The Plant. Leashed, well-behaved pets are allowed outside; pet policies may vary by individual business. The Plant is accessible to guests and will do its best to accommodate any additional requests. Please contact music@theplantnc.com with any accommodation requests or accessibility concerns. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Quiltmaker's Annual New Year's Open House
2026-01-01 13:00 - 16:00 | Quiltmaker Cafe, 75 W Salisbury St, Pittsboro, NC, 27312, United States
Join your community members and Quiltmaker Cafe for their Annual New Year’s Open House on Thu, Jan 1pm-4pm. Start 2026 right with desserts, games, and community at Quiltmaker’s future home (opening soon). This celebration is an Open-House, child-friendly event, so please stay for as long as you are able. Volunteer opportunities are available. Participating businesses include Circle City Ice Cream and bmc brewing.
No registration is required. Free parking is available on the street and in the public lot across the road. The space is ADA-compliant. No pets allowed.
