Jingle and Mingle with Chatham Pride Alliance
2025-12-18 18:00 - 21:00 (America/New_York) | 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.

Blues Jam at The MOD
2025-12-18 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
2025-12-19 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.

Last-Minute Christmas Market at The Plant
2025-12-19 15:00 - 20:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for a Last-Minute Christmas Market on Fri, Dec 19, 3pm-8pm. There will be fire pits, live music, local vendors selling handmade gifts, plenty of family fun, and food and drinks from the Plant’s tenants. 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.

Weekly Free Tastings at Vino!! Wine Shop
2025-12-19 17:00 - 19:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Weekly free tastings at Vino!! Wine Shop are hosted every Friday. Experts share their picks of wines with varied pricing and from diverse locations. Tasting details, including which wines will be served, are shared on their Facebook Page and in their newsletters.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

3rd Friday Artist Receptions
2025-12-19 17:00 - 20:00 | Pittsboro Gallery of Arts, 44 Hillsboro Street, Pittsboro, NC, 27312, United States
Pittsboro Gallery of Arts is pleased to announce the return of 3rd Friday Artist Receptions. Each month, they highlight a new artist and offer an opportunity to meet them and ask about their work. Beverages and snacks will accompany. These events are held every third Friday, 5pm-8pm. Featured artists are announced on their Facebook Page.
See more Pittsboro Gallery of Arts events.

Holiday Dinner at The Sycamore
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.

Run and Roam Fridays at The Plant
2025-12-19 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.

Live Piano Music at The Sycamore
2025-12-19 18:00 - 21:00, 2025-12-20 18:00 - 21:00, 2025-12-23 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.

Live Music: Geoff McBride at Havoc
2025-12-19 18:00 - 21:00 | North Carolina
Havoc Brewing Company presents Live Music with Geoff McBride on Fri, Dec 19, 6pm-9pm. 50 Kitchen food truck will be on-site at Havoc 5pm-9pm.
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.

Karaoke at Thirsty Skull
2025-12-19 19:00 - 21:00 | Thirsty Skull Brewing, 915 N Second Ave, Siler City, NC, 27344, United States
Join Thirsty Skull Brewing – Siler City on the third Friday of each month, 7pm-9pm for Karaoke with JV Jams.
See all events at Thirsty Skull Brewing. Part of the Chatham County Craft Beverages & Country Inns Trail.

Mystic Merry Market
2025-12-20 08:00 - 14:00 | Mystic Mocha, 111 Siler City Crossing, Siler City, 27344, United States
Come out to Mystic Mocha in Siler City for a Mystic Merry Market on Sat, Dec 20, 8am-2pm. There will be drinks, food, vendors offering last-minute Christmas gifts, and plenty of holiday magic! If you are interested in being a vendor, message them on Facebook or Instagram, call them at 919.799.7127, or stop by in person.
This event takes place indoors. Mystic Mocha is ADA-compliant. Free parking is available in front of the coffee shop. No pets allowed. See more events at Mystic Mocha.

Raclette and Wine Event at Vino!!
2025-12-20 15:00 - 18:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Travel with Vino!! Wine Shop to Savoie, France for a Raclette and Wine Event on Sat, Dec 20, 3pm-6pm. For $20, enjoy a plate of utterly divine Raclette – French Raclette cheese on a slice of bread with cornichons served by Alex Kast of Ulie’s Raclette, all perfectly paired with a glass of wine from Savoie. Please email anna@vinowineshopnc.com if you wish to attend.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Holly Jolly Christmas Party at House of Hops
2025-12-20 17:00 - 20:00 | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Join House of Hops for a Holly Jolly Christmas Party and their first-ever cookie exchange on Sat, Dec 20, 5pm-8pm. Wear your best ugly Christmas sweater and delight in a hot cocoa bar decked out with candy, marshmallows, chocolate, syrup, and more. Santa will be stopping by during the evening.
This event takes place indoors. House of Hops is pet-friendly. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Music: Stone Dolls at Havoc
2025-12-20 18:00 - 21:00 | North Carolina
Havoc Brewing Company presents Live Music with Stone Dolls on Sat, Dec 20, 6pm-9pm.
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.

The Graveyard Shift at The MOD
2025-12-20 20:00 - 23:59 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for The Graveyard Shift, a monthly dark disco dance party. All are welcome. This event is for ages 21+ and the cover is $5 per person. Upcoming event dates and guest DJs are listed below:

Sat, Jun 28, 8pm-12am Mouse the DJ.
Fri, Jul 18, 8pm-12am Guest DJ [SIN]APTIK.
Sat, Aug 16, 8pm-12am Guest DJ Ninjaficator.
Sat, Sep 13, 8pm-12am Guest DJ Baronovva.
Fri, Oct 31, 8pm-12am Guest DJ Lady Attercop.
Sat, Nov 22, 8pm-12am Mouse the DJ.
Sat, Dec 20, 8pm-12am Guest DJ That Darling DJ Duo.

See more events at The MOD.

Christmas Market at The City Tap
2025-12-21 11:30 - 15:30 | City Tap, 89 Hillsboro Street, Suite B, Pittsboro, NC, 27312, United States
Attention, last-minute shoppers! Join The City Tap for a Christmas Market on Sun, Dec 21, 11:30am-3:30pm. Get your host gifts, stocking stuffers, or spoil yourself, all while enjoying a cup of cheer! Vendors include:

Build-your-own cookie platters, breakfast pastries, and more from Confectious Creations.
Goat’s milk soap and skincare products from Toad Hollow Soapery.
Potted giant amaryllis, dried wreaths, Christmas ornaments, and other host gifts from Bumblebee Meadows.

On Sundays, enjoy $5 Bloody Marys and $4 Salty Dogs.
This event takes place at The City Tap. The patio is wheelchair accessible from the back of the building, and there is a lift to the second floor and the service area located on the secondary staircase that connects to the patio. See all events at City Tap.

Winter Solstice Sound Bath Journey + Rose Tea Ceremony with Maia Rhenish
2025-12-21 16:00 - 18:00 | North Carolina
Join Yoga Garden PBO for a Winter Solstice Sound Bath Journey + Rose Tea Ceremony with Maia Rhenish on Sun, Dec 21, 4pm-6pm. On the longest night of the year, come together to honor the winter season and the quiet light within. Join Maia Rhenish for a heart-centered gathering of sound and ceremony. The evening will begin with a rose tea meditation, opening your senses to the gentle, healing frequency of Rose. You’ll then flow into slow somatic movement and vocal toning, preparing the body and heart for an hour-long sound bath journey focused on the heart chakra. Bathed in Maia’s voice, gong, singing bowls, chimes, tuning forks, and drums, you’ll be guided into a space of inner peace and heartfelt connection. Together, embrace the darkness as a time to rest deep, reflect, and open to the returning light.
This class is $44 per person. Space is limited, so please preregister. See more events at Yoga Garden PBO.

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.

Euchre Mondays at bmc
2025-12-22 18:00 - 20:00 | bmc brewing, 213 Lorax Lane, Pittsboro, NC, 27312, United States
Join a fantastic group of Euchre enthusiasts every Monday, 6pm-8pm, for Euchre Mondays. This weekly gathering is built around the classic trick-taking card game. No experience is needed — a fantastic regular euchre group is happy to bring newcomers up to speed, so you can show up solo or with friends and jump right in. Monday doubles as $5 pint night at bmc brewing, so you can pair your hand of cards with one of the 18 beers bmc brews on site, alongside hard cider, hard seltzer, wine, and non-alcoholic options.
The event is free and takes place indoors. The space is wheelchair accessible, and on-site parking is free. Pets are not permitted indoors at bmc brewing. bmc brewing is part of The Plant. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Fearrington Farmers Market
2025-12-23 15:00 - 17:00 | Fearrington Farmers Market, E Camden, Pittsboro, NC, 27312, United States
The Fearrington Farmers Market is a producers-only market open Mar-Oct, Tuesdays, 4pm-6pm, and Nov-Feb, Tuesdays, 3pm-5pm, year-round in Fearrington Village. Bring reusable tote bags and plan to explore the many local vendors. You also might chat with the farmers, see old friends, or meet new ones! It’s a welcoming, inclusive, and friendly atmosphere that encourages healthy, happy living.
Fearrington Farmers Market has more than 3 dozen members and is now in its 30th season. Not all vendors are there every week, but some vendors are there every week, year-round. Each market features live music. Vendors include Celebrity Dairy, In Good Heart Farm, and bmc brewing. See their full list of vendors.
Come early if you’d like to review what is being offered; sales begin at the scheduled time, signaled by the bell. Bring along small bills ($20 or lower) to pay for your purchase. Some vendors accept credit and debit cards, and most will accept checks. This event takes place outdoors, rain or shine. Entry is free. Leashed, well-behaved pets are welcome. See more events at Fearrington Village.

Run Club at House of Hops
2025-12-23 18:00 - 20:00 | North Carolina
Join House of Hops every Tuesday, 6pm-8pm for Run Club and 20%-off mixed six pack. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Music Bingo at Hops and Berry
2025-12-23 19:00 - 21:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come to Hops and Berry-Pittsboro for Music Bingo every Tuesday, 7pm-9pm. Instead of numbers, players listen for tracks and mark their cards as they recognize each tune, racing to fill a line before anyone else. It’s a low-key, high-energy way to spend a weeknight, and the format welcomes everyone from casual listeners to die-hard music buffs.
This event is free and takes place indoors. Free parking is available onsite. This space is wheelchair accessible. Part of MOSAIC at Chatham Park. See more events at Hops & Berry. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Pub Trivia at Doherty's
2025-12-23 19:00 - 21:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for Pub Trivia every Tuesday, 7pm-9pm, hosted by Patrick W. Trivia. Trivia is free to play, with prizes for first, second, and third place.
See more events at Doherty’s.

Jennifer Curtis + Matthew Greenslade — A Special Holiday Double Bill
2025-12-23 19:30 - 21:30 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join Fair Game Beverage Company in the Wheelhouse for Jennifer Curtis + Matthew Greenslade — A Special Holiday Double Bill on Tue, Dec 23, 7:30pm-9:30pm. Jennifer Curtis returns for another Wheelhouse show, accompanied by Matthew Greenslade with festive Christmas tunes—plus some special guests! Matthew Greenslade will bring the holiday spirit and perform music from The Real Christmas Book! This is a show you don’t want to miss!
Composer and performer Jennifer Curtis has been described as a “multi-genre maverick” by the San Diego Union-Tribune. Her second solo concert in Carnegie Hall was described by the New York Times as “one of the gutsiest and most individual recital programs,” and she was celebrated as “an artist of keen intelligence and taste, well worth watching out for.” As a violinist, Jennifer has won the Milka-Astral Grand Prize for Violin, the Juilliard Concerto Competition, and competed in Austria at the International Brahms Competition. You can read her full biography here.
This event takes place indoors in the Wheelhouse. Tickets are $30 per person plus a $0.75 ticket service fee. 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.

Christmas Eve Party at Vino!!
2025-12-24 12:00 - 17:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Join Vino!! Wine Shop for a Christmas Eve Party on Wed, Dec 24, 12pm-5pm. Celebrate the end of the year and the holidays by wearing your ugly sweaters or Christmas PJs. There will be holiday cocktail specials and a cookie exchange! This event takes place indoors.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Music Bingo at House of Hops
2025-12-24 18:00 - 20:00 | North Carolina
Join House of Hops every Wednesday, 6pm-8pm for Music Bingo hosted by DJ Special K. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.
