The Corner Across From Pittsboro's Courthouse Is Back on the October Calendar

The building at 39 West Street has a curved front that faces the courthouse traffic circle. Out front are rows of outdoor chairs, a stage area and a wide patio. The Chatham Journal describes it that way, and for most of 2026 it stood empty in the middle of Pittsboro's downtown. Havoc Brewing closed there on December 14, 2025. Nonna's Café opened in the same space on September 18, 2026.

That gap lasted about nine months, and it ended just before October. This month, the arts walk ends on that patio. A week and a half later, the Rotary Street Fair fills the streets around it. The downtown calendar has a center again, and it sits directly across from the courthouse.

What moved into 39 West Street

Havoc opened in 2023 in a renovated part of the old Justice Motor Company property. It closed after about two years in business. The commercial listing described the space as roughly 8,494 square feet, renovated in 2023, with a custom bar, indoor seating and access to outdoor seating. A space that size facing the courthouse is hard to miss when it's dark.

Broker Eric Andrews told the Chatham Journal that the property drew several applicants. He said the tenants who got the lease stood out because they paired food with the site's social character and planned to open sooner than the others. Their plan comes in phases:

• Now: Nonna's Café, a coffee shop and wine bar open 7 a.m. to 5 p.m.
• Through the day: coffee and pastries in the morning, with wine later on.
• Next: La Cucina Della Nonna, a full-service Italian restaurant from owners Dana and Jim Rumbold. Chapelboro reports a target of spring 2027 for opening fully.

The plan matters most for what happens outside. The Chatham Journal reported that the patio and stage were designed as shared spaces for the whole SoCo property, not decoration. Andrews said the fire pit stays, the outdoor seating continues, and bands are expected to remain part of the concept. SoCo was planned as a connected dining and nightlife area. Its continuous deck lets people move between businesses without leaving the patio. So the reopening also gives downtown back its largest outdoor gathering space.

October 16 ends on the SoCo patio

The first test of that shared deck comes this Friday night. The Pittsboro Finally Fridays Arts Walk and Mask Parade runs Friday, October 16, from 5 to 8 p.m. It starts at the Pop-up Park at 50 W. Salisbury St., winds through the Social District and finishes with contests on the SOCO Patio at 39 West St., across from the courthouse traffic circle. The Town of Pittsboro calendar lists the same date, hours and starting point.

Nonna's is listed as open until 5 p.m., the same hour the walk begins. Anyone who wants coffee or a glass of wine inside before the route starts should plan for that. The parade's finish line is outdoors on the patio, so it doesn't depend on the café's hours.

A second event runs the same evening on the east side of town. MOSAIC at Chatham Park's calendar lists Blast from the Past Music Series: Y2K Kids on October 16 from 7 to 9 p.m. Since the walk starts two hours earlier, both fit in one evening. Spend the early hours downtown, then head to MOSAIC for the concert.

The weeks between, spread across three addresses

Between the arts walk and the Street Fair, the calendar spreads out. Most of it happens away from the Circle:

The Town lists Trails & Treats as an afternoon event, which makes it the daytime option for younger kids. The Plant's event calendar puts three nights in one week, and its Friday the 23rd market falls on the same date as MOSAIC's movie night. Friday the 30th is MOSAIC's turn, with a trunk-or-treat paired with the film. The next morning, the action moves back to the streets around the courthouse.

October 31 closes the loop around the Circle

The Pittsboro Street Fair runs Saturday, October 31, from 10 a.m. to 6 p.m. on Hanks, Fayetteville and Salisbury streets downtown. The Town's event listing says the Rotary Club of Pittsboro hosts it every year. It promises more than 100 vendors, food trucks, live music, family activities and a Trike Race. Admission is free, and a shuttle runs from Central Carolina Community College. The Rotary Club's own page describes the vendors as artisans, shops, nonprofits and food sellers, with kids' activities and live music all day.

The 2024 Chamber listing put that year's fair on October 26 and described more than 130 vendors. This year the fair falls on Halloween itself. Neither the Town nor the Rotary materials mention costume programming, so plan around the published schedule, not around Halloween traditions.

The fair's three streets surround the same few blocks the mask parade crosses two weeks earlier. For the first time this year, that stretch has an operating business on the courthouse-facing corner of 39 West Street. Nine months ago, a corner that size facing the main gathering point of downtown was empty.

The rest of Pittsboro's dining map is in motion too

The SoCo reopening stands out because so much else in town changed this season. Some changes shrink the list of places to eat, and others are still waiting to open.

Café Root Cellar ended restaurant service in mid-September. Its own announcement gave September 19 as the last day, and a later Chapelboro roundup said September 18. Chapelboro reported that the closing wasn't about popularity. Chef Sera Cuni and co-owner Susan White chose to put their effort into Feed-Well Fridges, a nonprofit that collects healthy, edible food from grocery store and restaurant partners and makes it available in free fridges around Chatham County.

Chatham Mills changed hands on September 3. Chapelboro reported that Chris Ehrenfeld, owner and CEO of BOLD Companies, bought the 28-acre property off Hillsboro Street and a 3.64-acre parcel to its north, for a total of nearly $12 million. The site has operated as a retail center since 1997. Its tenants include Chatham Marketplace, The Sycamore and the event space Forest Hall, and it hosts the weekly Chatham Mills Farmers Market from April through October. "Our first goal is to preserve and improve what is already here," Ehrenfeld told Chapelboro. He also said there are about 25,000 square feet to fill. October is the last month of the market's season, so the weekly market's first season under the new owner wraps up as the street fair arrives.

At MOSAIC, two openings are still pending as of mid-October. a Tavolo Italian Eatery at 367 Freedom Parkway, Suite 130, is listed on MOSAIC's dining page as "Coming Soon - October 2026." The menu centers on wood-fired pizza, handmade pasta and a full bar. Chapelboro reported on October 1 that the restaurant was close to a soft opening after a long buildout. It is a sister venture to The Sycamore and Forest Hall. Pecan Jacks Ice Cream · Candy Kitchen at 60 Mosaic Blvd., Suite 120, is listed as "Coming Soon - 2026." Neither had confirmed an opening date when this was written.

This fall, the Circle is the steadiest place to eat in town. One restaurant has closed, a shopping center is under new ownership with space to fill, and the new Italian spot on the east side hasn't opened yet. The café at 39 West Street is open, and the month's two big downtown days run right past it.

The first two weekends of November

The Pittsboro Business Association lists First Sunday for November 1, from noon to 4 p.m. at the Downtown Pop-Up Park, 50 W. Salisbury St., with live music, food trucks and artisans. It runs on the first Sunday of each month from April through December. The Pop-Up Park is also where the October 16 mask parade starts, a short walk from the SoCo patio.

The following Saturday, November 7, The Plant holds its 11th Annual Death Faire. That date ends a three-week run that begins this Friday on the patio across from the courthouse.

If you're watching how downtown Pittsboro is changing, from the SoCo reopening to the new ownership at Chatham Mills, Terra Nova Global Properties follows these openings and property changes as they happen. Let's Connect if you'd like to talk about what the changes around the Circle mean for your corner of town.