Live Piano Music at The Sycamore
2025-12-18 18:00 - 21:00, 2025-12-19 18:00 - 21:00, 2025-12-20 18:00 - 21:00 (America/New_York) | 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.

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.

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.

Line Dancing Classes at Chatham Mills
2025-12-19 11:00 - 12:00 | Forest Hall at Chatham Mills, 480 Hillsboro Street, Suite 350, Pittsboro, NC, 27312, United States
Build your skills on the dance floor with Line Dancing Classes at Chatham Mills, hosted by Forest Hall at Chatham Mills and the Chatham Social Club every Friday, 11am-12pm. The cost is $25 per class, and all skill levels are welcome; no partner is needed for class. Register now at chathamsocialclub.com – limited spots available! See more events at Chatham Mills.

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.

Create a Holiday Gnome with Checkered Tulip
2025-12-19 18:00 - 19:30 | Checkered Tulip, 35 West Chatham Street, Pittsboro, NC, 27312, United States
Join Checkered Tulip for a festive Create a Holiday Gnome workshop on Fri, Dec 19, 6pm-7:30pm. The cost for this class is $29 per person and includes hot cocoa and tea.
At Checkered Tulip, you’ll be on a machine making your project from the get-go. Their instructors are there to help you bring your vision to life and give you one-on-one access to all the tricks and hacks that make your project a breeze. This event takes place indoors. See more events at Checkered Tulip.

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.

Candleglow Sound Bath Meditation
2025-12-19 19:30 - 20:30 | Starrlight Mead, 130 Lorax Ln, Pittsboro, NC, 27312, United States
This night-time sonic ceremony is back by popular demand! Candleglow Sound Bath Meditation returns on the third Friday of each month from 7:30pm to 8:30pm at Starrlight Mead for a candle-lit evening sound bath featuring a variety of singing bowls, chimes, and percussion accompanying the human voice. Honoring seasonal cycles, Ancient Song Therapy crafts sonic landscapes conducive to relaxation, meditation, journey work, and integration.
This event costs $25 per person and is held indoors. RSVP is required. Please contact liodhruna@gmail.com for more information. Starrlight Mead is part of The Plant. The space is wheelchair accessible, with parking and entry available behind the production facility. Additional free parking is available on-site. Pets are not allowed. See all events at Starrlight Mead. See all events at The Plant. 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.

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.

Farewell Fall at White Pines
2025-12-20 14:00 - 17:00 | White Pines Nature Preserve, 548 S Rocky River Rd, Sanford, NC, 27330, United States
Join Triangle Land Conservancy for a Farewell Fall hike on Sat, Nov 20, 2pm-5pm at White Pines Nature Preserve. Say farewell to fall and explore the evergreen species still sticking around! It’s the last day of fall; all the leaves are gone… except evergreens! As we enter the coldest months of the year, learn to identify evergreen trees – it’s not just the five pine species of White Pines, but mountain plants such as rhododendrons and mountain laurel far outside their usual range. By the end of this hike, you should know how to identify all of them and the point where the Deep and Rocky Rivers meet. This will be a 3-mile hike that will end close to sunset. Flashlights and headlamps are suggested as the hike will end near dusk.
This is a free event, but registration is required. If registration is closed, please email Amaya Horner at ahorner@triangleland.org to be added to the waitlist.
CURRENT MASK POLICY
TLC seeks to build a supportive, mask-friendly environment in all collaborations with staff and the public. Please wear a mask if you are not vaccinated, or if that makes you feel most comfortable. We also encourage those eligible to receive their COVID-19 vaccine and booster shot. If you are experiencing any COVID-19-related symptoms, please stay home and attend the program on another day. Their top priority is to create a safe environment for our community. Thank you for your understanding.

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 Forest Bathing Walk
2025-12-21 13:00 - 14:15, 2025-12-21 14:30 - 15:45 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant and Rewild Within for a Winter Solstice Forest Bathing Walking on Sun, Dec 21, hosted:

1pm-2:15pm.
2:30pm-3:45pm.

Two sessions are available for this gentle, reflective experience to ground, express gratitude, and welcome the return of the light guided by Amy Allen. Connect with your senses, nature, and yourself- no experience needed. The session will end with a tiny tea ceremony and time to explore The Plant’s local shops and cafés. Don’t miss Rachel’s Native Plants for a living reminder of your walk. Limited spots are available. RSVP today to save yours.
ABOUT AMY ALLEN
After over a decade in ecology—working with thousands of volunteers across Colorado to restore lands impacted by floods and fires—Amy Allen felt called to combine her passions for nature, horses, and community. She became a certified Equine Gestaltist, Forest Therapy and Mindfulness Guide, and Executive Equine Facilitator, and founded Rewild Within. Through her work, Amy creates experiences that invite people to pause, reconnect, and rediscover their inner “yes.” She believes, “nature holds the answers we seek—because we are nature. Sometimes, we just need to slow down and remember.”
This event is free and will take place 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 not allowed for this program. See all events at The Plant.

Crafternoons at Clapping Hands Farm
2025-12-21 13:00 - 17:00 | Clapping Hands Farm, 3348 Alston Chapel Road, Pittsboro, NC, 27312, United States
Join Clapping Hands Farm for Crafternoons hosted every Sunday, December 2025-February 2026, 1pm5pm. This is a drop-in crafting circle, not a class. Bring a project you’re already working on, or join many of our crafters who are making items to donate to the Camp Store—a fun way to craft with purpose. You’re also welcome to come learn by doing; they’re happy to help folks get started, especially if it supports camp scholarships.
Classes usually take place at Clapping Hands Farm, unless otherwise posted, in their cozy, heated studio space. There is no fee to participate, but donations are welcome. Adults are welcome, and crafty teens may come solo. Children are welcome with a parent who can take full responsibility (the space is small and not ideal for toddlers). The camp store will be open during crafternoon sessions and by appointment through December and early January. All proceeds support camp scholarships. Come craft, connect, and help make camp accessible for more kids. Call 919.542.5599, email clappinghandsfarm@gmail.com, or send a WhatsApp message to RSVP. See more events at Clapping Hands Farm.

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.
