Wine and Swine Valentine's Dinner
2026-02-14 18:00 - 20:00 (America/New_York) | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Join Vino!! Wine Shop for a Wine and Swine Valentine’s Dinner on Sat, Feb 14, 6pm-8pm, crafted by Mackenzie Withington of Lilly Den Farm. Mackenzie is serving up a four-course meal, all of which will involve pork from her own animals on her farm. In keeping with Valentine’s Day, Sommelier Dom Decastro will present 4 wines (all rosé and red) that pair perfectly with the courses.
Only 36 spots are available. The cost is $100 per person, all inclusive with tax and gratuity. Please call 919.542.3922 or email anna@vinowineshopnc.com to make your reservations. Reservations must be made by Wed, Feb 11, at 3pm. You must provide your credit card information in order to hold the reservation.
MENU

First Course: Pork belly bites served with an apple slaw. NV Argyle Brut Rosé, Willamette Valley, Oregon.
Second Course: Creamy butternut squash soup with bacon end crutons. 2024 Li Veli’ ‘Askos’ Susumaniello Rosato, Puglia, Italy.
Third Course: Braised pork shoulder with stewed pinto beans and microgreens. 2022 Alto Moncayo Veraton Garnacha, Compo de Borja, Spain.
Fourth Course: Chocolate mousse topped with sea salt and bacon crumbles. 2023 Ancient Peaks Zinfandel, Paso Robles, California.

Please note: Since Vino!! is open for business this day, doors will not open until 6pm.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Live Piano Music at The Sycamore
2026-02-14 18:00 - 21:00, 2026-02-17 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.

Valentine's Champagne Wine Dinner at 458 West
2026-02-14 18:00 - 21:00 | 458 West Bed and Breakfast, 458 West St, Pittsboro, NC, 27312, United States
458 West B&B is excited to announce their Valentine’s Champagne Wine Dinner on Sat, Feb 14, 6pm-9pm. The cost is $155 per person or $395 per couple, and includes dinner, a room, and breakfast. The menu is listed below:

Apertif: Moet Imperial Brut Reserve.
Appetizer:

Legras & Haas Extra Brut Blanc de Blancs (NM – Côte de Blancs).
Marinated Shrimp with Champagne Beurre Blanc.

Salad:

Devaux Grand Réserve (CM Pinot Noir Dominant Blend – Côtes de Bar).
Poached pear and escarole salad, with savory croutons, goat cheese, and a Champagne vinaigrette.

Entree:

Vadin-Plateau Renaissance 100% Pinot Meunier (RM – Vallée de Marne BdN).
Sous Vide Lamb with roasted root vegetables and a Champagne Rosemary jus.

Dessert:

Boever Brut Rosé (RM Montagne de Reims).
Pink Champagne Cake with Vanilla Buttercream and strawberry ice cream.

Reserve your spot today! Send a DM or email them at innkeepers@458west.com. 458 West B&B is part of the Chatham County Craft Beverages and Country Inns Trail.

Brushes and Bubbles at House of Hops
2026-02-14 18:30 - 20:30 | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Join House of Hops for Brushes and Bubbles on Sat, Feb 14, 6:30pm-8:30pm. Come paint with your love. You and yours will each paint on your pre-sketched canvas, creating a completed masterpiece together at the end.
This fun date night is $65 per couple. Each ticket includes:

2 pre-sketched canvases with instructions.
2 drinks of your choice (wine/bubbles/beer).
Chocolate-covered strawberries.

Silhouettes are customizable to suit each couple. Arrive 30 minutes early to order your drinks! Wine & Design will have everything ready for you to create your very own masterpiece with your love. Event is NOT BYOB, discounts/coupons not valid. 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.
Cancellation Policy: All sales are final; no refunds will be issued if a customer cancels their reservation. To receive a credit, the customer must email ch@wineanddesign.com at least 24 hours before the event. Please note that if you are booking a reservation within 24 hours of the class, a credit will not be an option in the event you cannot attend class. If there is a threat of inclement weather or low attendance, the event may be canceled. If this is the case, you will be given credit for another class of equal value.

Valentine’s Day with Phantom Playboys at The MOD
2026-02-14 19:00 - 22:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for a Valentine’s Day with Phantom Playboys on Sat, Feb 14, 7pm-10pm. This is one of The MOD’s favorite bands and traditions. Come share the love!
This event takes place indoors at The MOD. Free parking is available on the street and across the road from the Government Annex Building, as well as in the Justice Center Parking lot. This space is wheelchair accessible. 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.

Winter Art Sale at the Vineyard
2026-02-15 12:00 - 17:00 | FireClay Cellars, 1276 Bowers Store Rd, Siler City, NC, 27344, United States
Join FireClay Cellars for a Winter Art Sale at the Vineyard. Winter is a little more inspiring! Browse an eclectic exhibition of fine art from the collections of Kate Ladd, Lucy Harris, and Wilma Schroeder while sipping a glass of wine. They’ll be open throughout the winter for the following hours:

Fridays, 11am-5pm.
Saturdays, 11am-5pm.
Sundays, 12pm-5pm.

Free parking is available on site. The porch and first floor are ADA-compliant, with wheelchair-accessible parking. FireClay Cellars is part of the Chatham County Craft Beverages and Country Inns Trail. Discover more events at FireClay Cellars.

Mead and Chocolate
2026-02-15 13:00 - 17:00 | Starrlight Mead, 130 Lorax Ln, Pittsboro, NC, 27312, United States
Bring your honey, friends, or Gal-entines for Mead and Chocolate to enjoy some chocolate paired with your tasting! $12 per person for 8 samples and two chocolates – no reservation needed! This event occurs on the following dates:

Fri, Feb 13, 12pm-6pm.
Sat, Feb 14, 12pm-6pm.
Sun, Feb 15, 1pm-5pm.

This event takes place indoors. Free parking is available on-site. Starrlight Mead is wheelchair accessible. No pets allowed. Starrlight Mead is part of The Plant. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Music with Mondo Guitaro at Vino
2026-02-15 14:00 - 16:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Join Vino!! Wine Shop and rebound after Valentine’s Day with Live Music with Mondo Guitaro on Sun, Feb 15, 2pm-4pm. “Lonesome Tones for High Plains Drifters,” Mondo Guitaro performs spaghetti western, surf, and 1960s style instrumentals arranged for two guitars. Drink specials all day, including $7 mimosas.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Galentine's Wreath Workshop at Buck Naked Farm
2026-02-15 14:00 - 16:00 | Buck Naked Farm, 1873 Chatham Church Road, Moncure, NC, 27559, United States
Enjoy a cozy, creative February afternoon at Buck Naked Farm’s Galentine’s Wreath Workshop on Sun, Feb 15, 2pm-4pm. Celebrate the season of friendship with a hands-on workshop that blends herbal goodness, dried florals, and a little kitchen magic. Together you’ll create practical, beautiful kitchen wreaths using fragrant culinary herbs, winter greenery, and a few dried blooms for texture and charm.
These wreaths are designed to be useful as well as beautiful—perfect for hanging near the stove, snipping sprigs as you cook, or adding a warm, handmade touch to your winter kitchen. Think rosemary, bay, thyme, sage… a wreath that smells incredible and actually earns its place on your wall. Bring a friend for a relaxed, joy-filled Galentine’s afternoon on the farm. No experience needed — just a love of cozy kitchens and good company.
Tickets are $99 per person and include all materials, flowers, supplies, and a special take-home favor bag, along with light refreshments and good company. Given the venue’s rural setting, the space is not ADA-compliant. This event takes place indoors. Free parking is available on-site. No pets allowed. See more Buck Naked Farm events.

Family-Friendly Mardi Gras Celebration
2026-02-15 15:00 - 18:00 | NC
Let the good times roll with Chatham Pride Alliance at their Family-Friendly Mardi Gras Celebration hosted on Sun, Feb 15, 3pm-6pm at Camp Royall in Moncure, NC. Get ready for a vibrant afternoon filled with Mardi Gras magic and fun for the whole family, including:

Games to delight all ages.
Delicious food inspired by Mardi Gras flavors.
Crafts to bring out your festive side, including opportunities to decorate a mini-float, design your own Mardi Gras mask, and make friendship bracelets.
A 360-degree photo booth to capture your best Mardi Gras poses.
Mardi Gras masks and beads to get into the spirit!

This inclusive, family-friendly event is free, open to everyone, and aims to bring the energy and excitement of New Orleans to Chatham County. Celebrate together in true Mardi Gras style – and don’t forget to dress for the occasion! Laissez les bons temps rouler!

President's Day Brunch at Carolina Brewery and Grill
2026-02-16 10:00 - 14:30 | Carolina Brewery & Grill, 120 Lowes Dr, Ste 100, Pittsboro, NC 27312, NC, 27312, United States
Visit Carolina Brewery and Grill for a President’s Day Brunch on Mon, Feb 16, 10am-2:30pm. Enjoy all your made-from-scratch brunch favorites and unbeatable drink specials, including $2 Mimosas, $5 Bloody Marys, and $10 Mimosa Mason Jars. Offerings include chicken and waffles, breakfast burritos and tacos, biscuits and gravy, and a classic low-country breakfast. For reservations, visit their website or call the restaurant directly.
Carolina Brewery & Grill is wheelchair accessible on the first floor. Free parking is available in front of the restaurant. Pets are welcome on the heated patio, which features fire pits, too. Part of the Chatham County Craft Beverages and Country Inns Trail. See all events at Carolina Brewery & Grill.

Euchre Mondays at bmc
2026-02-16 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.

St. Patrick's Day Celebration at Doherty's
2026-02-17 11:00 - 23:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for a St. Patrick’s Day Celebration on Sat, Mar 14, 12pm-11pm and Tue, Mar 17, 11am-11pm in downtown Pittsboro. Celebrate St. Patrick’s Day at your favorite neighborhood Irish pub with a two-day-long outdoor party, live Irish music, Irish food, Irish dancers, and live bagpipes that the whole family will love! The event lineup is as follows:
SAT, MAR 14, 2026

12pm: Live music with The Bucket Jam Band.
3pm: Irish Dance Performance with Triggle Academy of Irish Dance.
3:30pm: Live Music with Alibi.
6:45pm: Pipes & Drums.
7pm: Live Music with Nine Times Around.

TUE, MAR 17, 2026

5:30pm: Pipes & Drums.
6:30pm: Live Music with Tom Neuhauser.

These events take place outdoors. Doherty’s 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.

Fearrington Farmers Market
2026-02-17 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.

Mardi Gras Supper Club at The City Tap
2026-02-17 16:00 - 21:00 | City Tap, 89 Hillsboro Street, Suite B, Pittsboro, NC, 27312, United States
Join The City Tap for a special Mardi Gras Supper Club on Tue, Feb 17, 4pm-9pm. Celebrate Fat Tuesday with Gumbo and King Cake!
This event takes place at The City Tap. The patio is wheelchair-accessible from the back of the building. There is a lift to the second floor, and the service area is located on the secondary staircase that connects to the patio. See all events at City Tap.

Run Club at House of Hops
2026-02-17 18:00 - 20:00 | NC
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
2026-02-17 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
2026-02-17 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.

Coffee Klatch at Bynum Front Porch
2026-02-18 07:00 - 10:00 | Bynum General Store, 950 Bynum Rd, Bynum, NC, 27228, United States
Start your day with good coffee or tea and great conversation at Weekly Coffee Klatch with Bynum Front Porch Music, hosted every Wednesday, 7am-10am at the Historic Bynum General Store. Drop in for a warm cup, friendly faces, and casual community chats – everyone is welcome! Directions.
Year-round events, including a Christmas tree sale and a holiday bazaar. See a feature about geocaching in Bynum, produced by UNC-TV for NC Weekend and sponsored in part by the NC Division of Tourism, Film, and Sports Development. See more events at Bynum General Store.

Wake Up Wednesday at Carolina Brewery
2026-02-18 08:00 - 09:30 | Carolina Brewery & Grill, 120 Lowes Dr, Ste 100, Pittsboro, NC 27312, NC, 27312, United States
Wake Up Wednesdays are hosted at Carolina Brewery & Grill every third Wednesday, 8am-9:30am. This networking includes breakfast, coffee, and new guest speakers each month. The fee to participate is $7 cash or $8 by card. If you do bring cash, do your best to bring exact change. If you pay by check, make it out to the Carolina Brewery. Please consider bringing a tip for your server.
This event takes place indoors. The bottom floor of the brewery is wheelchair-accessible, including entrances, parking, and restrooms. See more events at Carolina Brewery & Grill.

Live Music at Galloway's
2026-02-18 17:00 - 19:00, 2026-02-19 17:00 - 19:00 | The Belted Goat, Market Street, Pittsboro, North Carolina, 27312, United States
Visit The Belted Goat/Galloway’s Bar at Fearrington Village, for live music, local beer on tap, and wine by the glass Wednesday-Saturday, 5pm-7pm. Check out their events calendar to see who’s playing.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.

Music Bingo at House of Hops
2026-02-18 18:00 - 20:00 | NC
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.

Crokinole at Fair Game
2026-02-18 18:00 - 20:00 | Fair Game Beverage Company, 192 Lorax Lane, Pittsboro, NC, 27312, United States
Try your hand at an obscure Canadian board game with Crokinole at Fair Game Beverage Company, hosted every third Wednesday, 6pm-8pm in the Wheelhouse. Crokinole is a classic Canadian tabletop game — think shuffleboard meets curling, shrunk onto a round wooden board. It’s easy to learn in a single round and genuinely fun whether you’re a first-timer or a seasoned shooter, and newcomers are always welcome.
Here’s how it works: Two players (or four, in teams) sit across from each other and take turns flicking small wooden discs from the outer edge toward the center of the board. The bullseye is a recessed hole in the middle worth 20 points; concentric scoring rings count for less the farther out you land. Guarding the center is a ring of eight small pegs that your disc has to navigate around.
If your opponent has any discs on the board, your shot has to hit one of them. Miss, and your disc is removed. If the board is clear, you have to land inside the innermost peg ring, or your disc comes off. So every turn is a choice between attacking your opponent’s pieces and quietly racking up points of your own. Discs are scored once all of them have been played, and the higher total wins the round.
Come early to 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.
Free parking is available on-site. This free event takes place indoors in the Fair Game Wheelhouse. Leashed, well-behaved pets are allowed outside; pet policies indoors 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. See all events at Fair Game Beverage Company. Part of the Chatham County Craft Beverages & Country Inns Trail.

Jazz Nights at The Sycamore
2026-02-18 18:00 - 21:00 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Every Wednesday night, 6pm-9pm, The Sycamore at Chatham Mills hosts live Jazz Nights every Wednesday, 6pm-9pm. The series features a rotating list of local musicians. The Sycamore also offers their Lounge Menu in the dining room on Wednesday nights. Reservations are highly recommended. Past and present musicians include the Steve Hobbs Trio, Lauren Meehan, Dave Quick Jazz, and the Tony Galiani Jazz Quartet. See the upcoming lineup here.

Karaoke at Hops and Berry
2026-02-18 19:00 - 22:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come out to Hops and Berry-Pittsboro for Karaoke every Wednesday, 7pm-10pm. The taproom’s weekly Karaoke night turns its live-entertainment stage over to the crowd, where regulars and first-timers alike line up to belt out their favorites—whether that’s a power ballad, a crowd-singalong anthem, or a deep cut only you remember. With a supportive, come-as-you-are vibe, it’s as fun to cheer from a table as it is to step up and perform.
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.

Run Club at Thirsty Skull PBO
2026-02-19 17:00 - 18:30 | Thirsty Skull Brewing – Pittsboro, 684 West Street, Pittsboro, NC, 27312, United States
Join Thirsty Skull Brewing – Pittsboro every Thursday, 5pm-6:30pm for Run Club.
See all events at Thirsty Skull Brewing – PBO. Part of the Chatham County Craft Beverages & Country Inns Trail.

Talks at The Plant: Preparing for the Storm
2026-02-19 18:00 - 19:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Talks at The Plant: Preparing for the Storm on Thu, Feb 19, 6pm-7pm. Join Trip Overholt and friends for a timely, grounded talk on resiliency preparation—how individuals and communities can stay steady, connected, and ready in the face of extreme weather events and periods of political unrest. Drawing on real-world experience and practical tools, this conversation explores preparedness beyond panic: building adaptable systems, strengthening local networks, and cultivating the mental and emotional resilience needed to navigate uncertainty with clarity and care.
Come early or stay late for a chance to 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.
Free parking is available on-site. The free event takes place indoors in the Wheelhouse at Fair Game Beverage Company. Pets are not allowed. 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.

Opinionation Trivia at House of Hops
2026-02-19 18:00 - 20:00 | 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.
