Pittsboro-Siler City Convention & Visitors Bureau

Opinionation Trivia at House of Hops
2025-12-11 18:00 - 20:00 (America/New_York) | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Join House of Hops every Thursday, 6pm-8pm for Opinionation Trivia. This Family Fued-style trivia game is so much fun! Play at 6pm and again at 7pm for two chances to win $15 or $25 House of Hops gift cards. Bring the crew, bring food from neighbors Cafe Root Cellar or Mi Cancun, and enjoy!
More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Piano Music at The Sycamore
2025-12-11 18:00 - 21:00, 2025-12-12 18:00 - 21:00, 2025-12-13 18:00 - 21:00 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Every Tuesday, Thursday, Friday, and Saturday night, 6pm-9pm, The Sycamore at Chatham Mills hosts live Live Piano Music. The series features a rotating list of local musicians. Past and present musicians include Kris Whitenack, Robert Griffin, Lindsey Rosebrook, and Stephanie Schmitt. See the upcoming lineup here.
See more events at The Sycamore at Chatham Mills.

Billecart-Salmon Champagne and Caviar Dinner
2025-12-11 18:30 - 21:00 | Fearrington House Restaurant, 230 Market Street, Pittsboro, 27312, United States
Reserve your spot for Fearrington’s Billecart-Salmon Champagne and Caviar Dinner on Thu, Dec 11, 6:30pm-9pm. Fearrington is proud to partner with Pierre Chichportiche of the historic house of Billecart-Salmon Champagne for a memorable evening of bubbles and caviar! Rooted in its ancestral motto ‘Give priority to quality, strive for excellence’, the environmental philosophy of Maison Billecart-Salmon is based on a long-term vision, with respect for nature and for future generations. Billecart-Salmon was certified for Sustainable Viticulture in Champagne in 2017. Today, around 100 hectares are also managed with organic agriculture, including 10 hectares converted to biodynamic viticulture. Select Champagnes will be paired with caviar-focused custom dishes created by Chef Paul Gagne.
This $295 wine dinner is non-refundable and totals $385 with tax and service. If you want overnight accommodations, please contact Fearrington House Inn at 919.542.2121. Please note: they cannot refund ticket purchases. If your plans have changed, please feel free to send a lucky friend in your place – just email them with their name or have them bring your confirmation email.
ABOUT PIERRE CHICHPORTICHE
Originally from Saint-Malo, France, and later based in the French Riviera, Pierre holds a Master’s degree in Business & Marketing and a WSET Level 3 certification. He has over 12 years of experience in wine sales and brand management in the United States. Since 2019, he has served as Eastern U.S. Director for Champagne Billecart-Salmon, overseeing sales strategy and market development across the region. Based in New York City since 2012, he is passionate about wine and has a strong appreciation for gastronomy, travel, boxing, and motorcycling.
Hosted by Fearrington House Restaurant. See more events at Fearrington Village. Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail.

Blues Jam at The MOD
2025-12-11 19:00 - 22:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for Blues Jam hosted every Thursday, 7pm-10pm by Lo Taylor. This open jam is an excellent opportunity for those who share a love for the blues and wish to share their talents. Mr. Taylor and his band of talented musicians will make you feel right at home on our stage. Bring your voice, bring your instruments, or just bring your ears to partake in this musical delight. The Mod is dedicated to providing space for live music, great food, craft beverages, community, and love. Arrive early for musician sign-up or to grab a table for the evening. Any schedule changes due to weather, holidays, or unforeseen circumstances will be posted on their Facebook and Instagram pages.
See more events at The MOD.

Jordan Lake Farms - Winter 2025 Season
2025-12-12 09:00 - 17:00, 2025-12-13 09:00 - 17:00, 2025-12-14 09:00 - 17:00 | Jordan Lake Farms, 2170 Marthas Chapel Rd, Apex, NC, 27523, United States
Join Jordan Lake Farms for their Winter 2025 Season, hosted on select weekdays and weekends in November and December. Shop their choose-and-cut field, register for a wreath-making workshop, and savor hot chocolate and mini donuts from the concessions stand. Plus, there are plenty of fun activities for the kids, including a hayride and a children’s play area. You can also choose from fresh-cut NC Fraser Firs, NC White Pines, and Concolor Firs, as well as Ball and Burlap trees that can be planted after Christmas. They are open on the following dates:

Sat, Nov 22 and Sun, Nov 23, 9am-5pm.
Wed, Nov 26, 8:30am-1:30pm.
Fri, Nov 28-Sun, Nov 30, 8am-6pm.
Wed, Dec 3 and Thu, Dec 4, 9am-5pm.
Fri, Dec 5, 9am-6pm.
Sat, Dec 6 and Sun, Dec 7, 8am-6pm.
Wed, Dec 10-Sun, Dec 14, 9am-5pm.
Wed, Dec 17-Fri, Dec 19, 9am-5pm.

Please note that offerings may vary depending on the date of your visit. Please check their website first before planning your visit.
Reservations will be required (at no fee) to visit the farm during Thanksgiving weekend (Nov 28-30) and the following weekend (Dec 6-7). Please note, reservations are required even if picking up a previously tagged tree. The reservation system will open the first week of November. Although reservations are not required during opening weekend (Nov 22 & 23), please note that parking is limited, and there may be periods when they cannot accommodate additional visitors.
Pets are welcome on the farm if on leash and are well-trained. Photographers and their clients are allowed by appointment at their farm. Please see the Photographer page of their website for details. They accept cash, credit, and Apple Pay. See more events at Jordan Lake Farms.

Annual High-End Wine Tasting at Vino!!
2025-12-12 17:00 - 19:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Join Vino!! Wine Shop for their Annual High-End Wine Tasting on Fri, Dec 12, 5pm-7pm. This is one event their customers look forward to every year! Two of their favorite wine reps, Ian Spotz of Advintage Distributing, and Mike Ruocco of Monsieur Touton, will be in the shop pouring 8 wines priced from $30 to $80. The wine lineup will be announced the week of Fri, Dec 12. The cost is $5 per person.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Run and Roam Fridays at The Plant
2025-12-12 17:00 - 21:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant after work and/or school for Run and Roam Fridays, hosted every Friday evening, Sep 5-Dec 12, 5pm-9pm. Come out for food and drink specials and plenty of family-friendly fun, including games, hula hoops, bubbles, chalk art, and more. Sip and shop the Chatham Beverage District, part of the Chatham County Craft Beverages & Country Inns Trail, with local beers from bmc brewing, wines and ciders from Starrlight, spirits from Fair Game, and sake from Koshu. Local dining available at Kingston 99 Kitchen and Ta Contento.
This free event takes place 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. Leashed, well-behaved pets are allowed outside; pet policies may vary by individual business. See all events at The Plant.

Wine and Design: Holiday Wreath-Making at For Garden's Sake
2025-12-12 18:00 - 19:30 | For Garden’s Sake, 9197 Hwy 751 S, Durham, NC, 27713, United States
Join For Garden’s Sake for Wine and Design: Holiday Wreath-Making on Fri, Dec 12, 6pm-7:30pm. Get ready for a magical evening event as you celebrate the holidays and creativity, surrounded by the glow of twinkle lights. This after-hours wreath-making workshop is designed for those who love to relax with crafts, snacks, and a good glass of wine.
You’ll begin with some guided instruction from FGS Plant Coach Debbi Barrett, then let your creativity flow as you bring your own style to a beautiful, fresh 20-22″ wreath. Whether your style is natural and woodsy or bright and festive, you’ll leave with a custom piece you’ll be proud to hang on your door! As you craft, sip a seasonal drink specially created for the evening, munch on the cheese and charcuterie spread, and enjoy a sweet treat.
Space is limited for this intimate evening event. Reserve your spot and start your holidays with a little spark and a lot of creativity! The fee is $95 per person and includes all necessary supplies and materials, a seasonally-inspired cocktail, cheese and charcuterie, and dessert. Non-alcoholic beverages are also available. Payment at the time of registration is required to hold your spot.
This class will take place indoors at the Robin’s Nest. Free parking is available on site. No pets allowed. See more events at For Garden’s Sake.

Live Music: Leonardo Braswell at Havoc
2025-12-12 18:00 - 21:00 | NC
Havoc Brewing Company presents Live Music with Leonardo Braswell on Fri, Dec 12, 6pm-9pm. Taco Paraiso food truck will be on-site at Havoc 5pm-8pm.
This event is free and will take place both indoors and outdoors, weather permitting. There is no cover for entry, but tips for the musicians are encouraged. Free parking is available in the lot across the street. Pets are welcome. This space is wheelchair accessible. More events at Havoc Brewing Company. Part of the Chatham County Craft Beverages & Country Inns Trail.

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.

Holiday Arts and Crafts Street Fair
2025-12-13 11:00 - 15:00 | Moncure Haywood Community, 1855 Old US 1 Highway, Moncure, 27559, United States
It is the most wonderful time of the year! Come to Moncure for an incredible transformation of Old US 1 into a holiday wonderland at the Holiday Arts and Crafts Street Fair on Sat, Dec 13, 11am-3pm. Stroll Old U S 1 and experience the magical spirit with pop-up vendors such as Seven Springs Winery, food, live music, a Polar Express Train, shopping, and more. Are you known for your baked goods, homemade goodies, crafts, and retail items? Would you like to market and expand your organization/business reach to the community? They have a booth reserved just for you! They’ve also added the Holiday Car Show! Showcase trophies will be presented to the winners. Early Bird Car Show entry cost is only $10. Entries submitted on the day of the event will be $15.
This event is sponsored by Moncure-Haywood Events Organization. Admission is free. This event takes place outdoors. Free parking, including handicap parking, will be provided. Leashed pets are allowed, but discouraged.

Christmas in Bennett
2025-12-13 11:00 - 19:00 | Bennett, 52-68 W Raleigh 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.

Tasting Classes with EB Wines
2025-12-13 14:00 - 15:00 | EB Wines, 40140 Moring, Chapel Hill, 27517, United States
The seventh annual Wine Tasting Classes is a collection of monthly wine tasting classes hosted by Esteban Brunello, owner of EB Wines. The classes are informative yet relaxed and open to guests with varying levels of knowledge, from novice wine drinkers to seasoned tasters. Classes are led by owner and wine director Esteban Brunello, who guides guests through the wine tasting process. Guests will learn to identify various wine notes, discover techniques in the winemaking process, and receive recommendations for food pairings.
Mark your calendars for the following class dates:

Sat, Jul 26, 2pm-3pm Refreshing Whites.
Sat, Aug 23, 2pm-3pm Skin Contact.
Sat, Sep 20, 2pm-3pm Domestic Wines.
Sat, Oct 18, 2pm-3pm Obscure Reds.
Sat, Nov 15, 2pm-3pm Fall Reds.
Sat, Dec 13, 2pm-3pm Sparking – Petillant Naturel.

EB Wines is part of the Chatham County Craft Beverages & Country Inns Trail. See all events at EB Wines.

Champagne Tasting at Vino!!
2025-12-13 14:00 - 16:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Join Vino!! Wine Shop for a unique Champagne Tasting on Sat, Dec 13, 2pm-4pm. Axel Kjellerman of A-Vin-Garde will be at Vino pouring 4 respectable, grower Champagnes that will blow you away! We all need that perfect bottle of bubbly to celebrate the holidays with! Cost is $10 per person and gets you a taste of all four wines plus some delightful nibbles that pair wonderfully with Champagne. If you love a bottle – pop one open and drink it on the spot (no corking fee)!
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Christmas Tea at O'Kelly Chapel
2025-12-13 14:00 - 17:00 | O’Kelly Chapel, 9197 NC-751, Durham, 27713, 27713, United States
Join For Garden’s Sake and O’Kelly Chapel for Christmas Tea on Sat, Dec 13, 2pm-5pm. This event is designed for those seeking an afternoon of tranquility amid the holiday hustle and bustle. Relax into your seat as you sip on a lovely cup of tea. Indulge in sweet and savory delicacies and good company. Appreciate the gleam of sunlight pouring through the Chapel windows, and admire the beautiful houseplants and Christmas trees tucked into every corner.
Christmas Tea at O’Kelly Chapel will be an afternoon to remember. There is no better way to celebrate the holidays with those you hold dearest!
They will have a fixed menu and cannot accommodate every dietary restriction. However, they can accommodate gluten-free requests and a few other allergies. Please inquire before booking if you are concerned about a specific allergen or restriction. The fee is $75 per person and is reserved by table. Pricing includes a selection of specially selected teas in classic and seasonal flavors, as well as sweet and savory delicacies. Space is limited for this intimate afternoon event. Reserve your spot today! Payment at the time of registration is required to hold your spot.
This class will take place indoors. Free parking is available on site. No pets allowed. See more events at For Garden’s Sake.

Christmas Celebration at Silk Hope Farm Heritage Park
2025-12-13 14:00 - 17:00 | Silk Hope Farm Heritage Park, 4221 Silk Hope Rd, Siler City, NC, 27344, United States
Join Silk Hope Farm Heritage Park for a Christmas Celebration on Sat, Dec 13, 2pm-5pm. Santa will arrive at 2:30pm on the Farm Heritage Park grounds, accompanied by a special guest! Bundle up the kiddos and come on out to have your picture taken with Old Kriss Kringle. There will be lots of other fun for the whole family, including kiddie train rides, hot chocolate, a bouncy house, letters to Santa, face painting (fee), and a cake walk. Be sure to stick around for the lighting of the wagon at 4:30pm. A free special drawing will take place at the wagon (must be present to win).
For more information, contact Missy Thompson at 336.622.5493. See more events at Silk Hope Farm Heritage Park.

Wreath-Making Workshops at Jordan Lake Farms
2025-12-13 14:30 - 17:00, 2025-12-14 14:30 - 17:00 | Jordan Lake Farms, 2170 Marthas Chapel Rd, Apex, NC, 27523, United States
Join Jordan Lake Farms for Wreath-Making Workshops, hosted on select dates in November and December. Their skilled farmers will guide you in crafting an exquisite Christmas wreath while you learn the artistry of transforming greenery into stunning festive decor. The wreath workshop includes beautiful greenery, a bow, a wreath ring, and wire to finish a wreath that is 18-26 inches in diameter – perfect for most commonly-sized doors. Bring a pair of garden clippers and plastic or cardboard to lay your finished wreath on, as sometimes sap can drain from fresh-cut greenery. Workshops take place on the following dates:

Sat, Nov 22, 2:30pm-5pm.
Wed, Nov 26, 10:30am-1pm.
Wed, Dec 3, 9:30am-12pm.
Thu, Dec 4, 2:30pm-5pm.
Thu, Dec 11, 9:30am-12pm.
Sat, Dec 13, 2:30pm-5pm.
Sun, Dec 14, 2:30pm-5pm.

This workshop is suitable for ages 13 years and older. Attendees aged 13-15 must be accompanied by an adult to participate in the workshop. Workshops will be 2-3 hours long. The number of workshop attendees will be between 5 and 15, depending on the project. If fewer than 5 attendees are registered 48 hours before the workshop, the workshop will be cancelled.
Registration is required for this event. You will be asked to pay in full to reserve your spot for the workshop. Workshops are rain or shine and non-refundable. This event takes place in Jordan Lake Farm’s new “Hide-Away Pavilion”. Parking will be in the lot closest to their tree field, with directional signs posted. See more events at Jordan Lake Farms.

Live Music at The Plant: Rose and Carole
2025-12-13 15:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Rose and Carole on Sat, Dec 13, 3pm-6pm. Jordan Napoli-Cranford is a local musician who grew up just down the road in Robbins. She has been performing in various musical groups since 2016. As for her sound, she loves to cover a range of genres and does everything from Adele to Led Zeppelin. She also performs in a musical duo with her wife, Amanda, called Rose & Carole.
There is no cover for music, but tips for the musicians are encouraged. Most events are rain or shine; if they have to cancel, they will try to do so well in advance. 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. Leashed pets are allowed. This event is free! See all events at The Plant.

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.

Live Music: Downpour at Havoc
2025-12-13 18:00 - 21:00 | NC
Havoc Brewing Company presents Live Music with Downpour on Sat, Dec 13, 6pm-9pm. Jessica’s Cheesesteaks food truck will be on-site at Havoc 3pm-8pm.
This event is free and will take place both indoors and outdoors, weather permitting. There is no cover for entry, but tips for the musicians are encouraged. Free parking is available in the lot across the street. Pets are welcome. This space is wheelchair accessible. More events at Havoc Brewing Company. Part of the Chatham County Craft Beverages & Country Inns Trail.

Brunch with Santa at Doherty's
2025-12-14 11:00 - 13:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for Brunch with Santa on Sun, Dec 14, 11am-1pm. This festive lunch with Santa will feature good food, big smiles, and all the cozy cheer of the season. Settle in for a relaxed meet-and-greet, snap your own photos, and enjoy the moment at your own pace. It’s an easy, joyful way to share a meal, make memories, and soak up a little holiday magic together!
This event takes place indoors. Doherty’s first floor is wheelchair accessible and offers accessible seating. Free public parking is available just across the street. Leashed pets on the patio only, please. See more events at Doherty’s Irish Pub & Restaurant.

Live Music at The Plant: The Overtones Sax Quartet
2025-12-14 12:30 - 15:30 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with The Overtones Sax Quartet on Sun, Dec 14, 12:30pm-3:30pm. The Overtones are a Sax quartet located in the Apex & Holly Springs. If you missed their Christmas set last year, you don’t want to miss this one!
There is no cover for music, but tips for the musicians are encouraged. Most events are rain or shine; if they have to cancel, they will try to do so well in advance. 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. Leashed pets are allowed. This event is free! See all events at The Plant.

FireClay Cellars Ornament Party
2025-12-14 13:30 - 16:00 | FireClay Cellars, 1276 Bowers Store Rd, Siler City, NC, 27344, United States
Join FireClay Cellars for an Ornament Party on Sun, Dec 14, 1:30pm-4pm. Start getting ready for the holidays by painting three beautiful wooden ornaments—perfect for your tree or as gifts! The cost is $45 per person and includes a glass of FireClay’s wine. You must pre-register for this event.
FireClay Cellars is part of the Chatham County Craft Beverages and Country Inns Trail. Discover more events at FireClay Cellars.

Paint + Sip at Vino!! Wine Shop
2025-12-14 14:00 - 16:30 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Join Vino!! Wine Shop for their Paint + Sip on Sun, Dec 14, 2pm-4:30pm, led by artist Lyanne Spangler of Sirlsly Art. This time around, you’ll have the opportunity to hone your painting skills on a holiday-inspired painting! Her classes are very popular, so hurry and sign up to avoid missing out.
The cost for this event is $42, which includes all painting supplies and one drink. Space is limited to 17 people. Register by phone at 919.542.3922 or email anna@vinowineshopnc.com by Thu, Dec 11. No refunds will be issued for cancellations after this date, as all supplies will have been purchased.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Raclette Party at The Plant
2025-12-14 14:00 - 17:00 | Fair Game Beverage Company, 192 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for a Raclette Party hosted by Alexander Kast on Sun, Dec 14, 2pm-5pm. Raclette is a traditional dish of the European Alps and literally translates to “scrape” from French. It describes the act of scraping off (or Racletting) the bubbly, lightly browned layer of molten cheese that has been slowly broiling underneath the Raclette Grill. The fragrant, savoury cheese is layered on top of local sourdough bread, sprinkled with salt and pepper, and accompanied with cornichons.
This event takes place indoors in Fair Game Beverage Company’s Wheelhouse. 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 not allowed. See all events at The Plant.
