The cranberry curried chicken salad from Quality Street Kitchen and Catering is still available in Leonardtown. It just comes from a different kitchen now. In mid-September, The BayNet reported that Jen Purcell and her mother, Sharon, have retired Quality Street after more than 20 years. Purcell is joining Kelly Davin at Kneaded Baking Co. to build a rotating menu of sandwiches, salads and other savory dishes. The chicken salad is coming with her, and so are Quality Street's refillable olive oils and balsamic vinegars.
That handoff fits the rest of Leonardtown's year. Most of the downtown businesses that opened in 2026 moved into a space someone else had just left, or moved themselves to a bigger one. A lot of those moves lead to the same building, and that building is where the busiest weekend of the fall calendar gets going.
The chain of handoffs
Follow this year's moves from space to space, rather than by date, and each one hands off to the next. In February, the Leonardtown Business Association's update read almost like a moving schedule.
- Smash House moved out of Shepherd's Old Field Market to a new location at 41656 Fenwick St. It began a soft opening at the end of January and was fully open with a ribbon-cutting behind it by mid-February.
- Bowl 29 took over the space Smash House left inside Shepherd's Old Field Market at 22725 Duke St. It held a storefront ribbon-cutting on Aug. 14. It serves fusion-inspired comfort food and still runs its food truck.
- Domoishi began a soft opening on Feb. 10 in SIP's former space at 22845 C Washington St., near the Dunkin'. It serves poké bowls, ramen, wings and boba.
- Kneaded Baking Co. announced in February that it would move to a larger space in the historic Old Bell Motor Company building. It held a ribbon-cutting at 22675 Washington St. in April.
- What The Fizz Beverage Boutique opened Aug. 7 at 22699 Washington St., in the space Kneaded left behind. The menu covers dirty sodas, matcha, energy drinks, teas, coffee and boba.
- The Vintage Collective held its grand opening March 7 at 22765 Washington St., in the former Kenny's Flowers space.
Noli's Italian Cucina is a handoff of another kind. The address stayed the same and the ownership changed. The new owners kept the original recipes and the dining room, added a larger dining area, and began Monday service on March 9.
A few changes started before this year. SIP Cafe closed in fall 2025, which opened the space Domoishi now uses. Everyday Saint Brewhouse opened its downtown taproom in December 2025, so this fall is its first on the square. One producer left town. Jubilee Farm Fermentations moved its operations to Historic St. Mary's City early this year and now goes by The Farthings Fermentery.
Add it up and the square's business mix is noticeably bigger than a year ago. But very little of that came from new construction or empty lots filling in. Existing spaces got passed along, and Kneaded moved into a larger space nearby.
Why the Bell Building matters now
Two of those threads end at 22675 Washington St. Kneaded's new home is there. Town Market is also listed at that address, in Unit 106 of the Bell Building, and it hosts the First Saturday Market series.
The Quality Street news adds to that. Kneaded moved there as a bakery. Now it's also where Purcell is cooking savory food and where the refillable oils ended up, so a stop there covers more than dessert. Put a Saturday market in the same building and the Bell Building becomes a natural first stop on a downtown morning.
That matters most on the first weekend of October.
October 2–4, laid out by address
Leonardtown's First Fridays run all year. From May through October, they stretch into full weekends. This year's October theme is Octoberfest, Oct. 2–4, and it's the last all-weekend version of 2026. November 6, "Passport to the Holidays," goes back to a single evening, and so does December 4, "Gingerbread Lane." The town's event page describes Octoberfest as a townwide celebration with participating downtown businesses, galleries, restaurants and shops, without naming them or listing hours.
What is on the calendar so far:
| When | What | Where |
|---|---|---|
| Fri., Oct. 2, 5–8 p.m. | "A Harvest of Haunts" opening reception, St. Mary's County Arts Council | 22660 Washington St. |
| Fri., Oct. 2, 5–7:30 p.m. | Free, all-ages pop-up watercolor activity | Arts Council |
| Fri., Oct. 2, starting 5 p.m. | Audience-participation drum circle, followed by a drumline performance | Arts Council |
| Sat., Oct. 3, 9 a.m.–4 p.m. | First Saturday Market | Town Market, the Bell Building, 22675 Washington St., Unit 106 |
| Oct. 3–31 | Scarecrow Stroll | Downtown streets |
| Oct. 2–4 | Octoberfest First Friday Weekend | Participating downtown businesses |
Friday evening centers on the Arts Council's block. Saturday morning moves to the Bell Building, where the market lists vendors selling produce, meats, cheeses, breads, desserts, flowers, plants, clothing and shoes. Kneaded is in the same building. The Scarecrow Stroll opens the same Saturday, with displays along downtown streets and voting for favorites through the end of the month.
That puts this year's openings on one short walk. From the Bell Building, What The Fizz is also on Washington Street, at 22699, in Kneaded's old space. The Vintage Collective is at 22765 Washington St. Domoishi is at 22845 C Washington St. Bowl 29 is around the corner on Duke Street at Shepherd's Old Field Market, and Smash House is over on Fenwick. Last October, several of those addresses had different names on the door. Some of these businesses weren't downtown yet.
No street-closure notice for the weekend had been posted in the sources we checked. The town's event page is the place to check for any late logistics.
Before and after the long weekend
This Sunday, Sept. 27, is the second annual Paw Crawl. It started in 2025.
Two weeks after Octoberfest, the calendar moves from the square to the fairgrounds. The 60th U.S. Oyster Festival, home of the U.S. National Oyster Shucking Championship, runs Oct. 17–18 at the St. Mary's County Fairgrounds, 42455 Fairgrounds Road. Hours are 10 a.m. to 6 p.m. Saturday and 11 a.m. to 6 p.m. Sunday. Tickets are:
- $15 for a one-day adult ticket
- $5 for youth ages 6 to 17
- Free for children 5 and under
- $25 for an adult two-day pass
The Rotary Club of Lexington Park hosts, and advance tickets are on sale through usoysterfestival.org.
The Scarecrow Stroll is still up downtown that weekend. It runs through Oct. 31, so the displays are there for the festival weekend and the rest of the month. After that, First Friday goes back to one evening on Nov. 6.
A few things were still unknown as of Sept. 23. We haven't seen a confirmed final service date for Quality Street or a named vendor list for the Oct. 3 market. We also haven't seen a confirmed 2026 opening at Leonardtown Wharf. For now, this year's changes are all on and around the square.
If you live near the square, you've watched these storefronts change all year. If you're wondering what that walkable, busier downtown means for your home's value, Prestige Home Team can give you a local read on it. Get Your Instant Home Valuation, and we'll walk you through how nearby homes are selling.
