The first Longwood Arts & Crafts Festival ran on two afternoons, December 3 and 4, 1977. It had art vendors, food booths and music performers, and the Longwood Historic Society calls it "a huge success." The group running it was then called the Central Florida Society for Historic Preservation, and the festival was a fundraiser.
Four years earlier, in 1973, two old houses had been moved from Altamonte Springs to the blocks where the festival still sets up. On November 21 and 22, the 50th annual festival fills those same streets. Longwood's oldest landmarks, its biggest weekend and even its best-known wing house all have something in common. They have lasted by moving to new addresses and new hands.
The Festival Was Built Around Buildings That Arrived by Truck
The Bradlee-McIntyre House at 130 W. Warren Ave. was designed for Boston architect Nathaniel J. Bradlee. Research cited by the Society dates its construction to 1885 through 1888. It came to Longwood from Altamonte Springs in 1973.
The Inside-Outside House at 141 W. Church Ave. is older still. It dates to 1873 and is known for its exposed exterior framing. The Society moved it from Altamonte Springs to its current spot the same year, 1973. Today it houses the Cottage Gift Shop, which says it has operated from that storefront for more than 39 years.
The district's grand old hotel, the Longwood Inn at 300 N. Ronald Reagan Blvd., changed hands before it was even finished. Town founder Edward Warren Henck commissioned it in 1883, and it was mainly completed in 1885. Carlos Cushing bought it, finished construction in 1886 and named it The Waltham. It has had several names since then. It reopened as the Longwood Hotel in 1910 and became the Longwood Village Inn after a 1972 purchase.
So the order went like this. The houses arrived in 1973, and the festival followed in 1977 as the preservation society's fundraiser. For decades, the event and the buildings were run from the same place.
Forty Years of Volunteers, Then a Handoff
The Society ran the festival as its main fundraiser for about 40 years. Its own account of that stretch is short:
"It was a lot of work! The festival committee worked on it almost year-round, using a second-floor office in the Bradlee-McIntyre House as their base of operations."
That comes from the Society's history of the festival.
In 2017, the City of Longwood asked to take over running the show. The Society agreed to the city's terms on the condition that royalty payments would continue. Without the year-round workload, the Society began starting other events, beginning with the Longwood Monster Dash 5K in 2018.
That handoff explains how November works around the Historic District now. The city produces the big weekend, and the preservation group that started it still receives royalties. The Society now spends its volunteer time on smaller events held in and around the two houses. The Society's calendar for the rest of the year shows the result:
- November 2026 Car Show: Saturday, Nov. 14, 4 to 8 p.m., at the Longwood Historic Civic Center, 135 W. Church Ave.
- Carols & Cocoa: Saturday, Nov. 28, 3:30 to 6 p.m., at the Bradlee-McIntyre House Museum and the Historic Civic Center. Tickets are sold in advance.
- 7-Foot Santa: Saturday, Dec. 12, 11 a.m. to 2 p.m., at the Bradlee-McIntyre House Museum.
- December Car Show: Saturday, Dec. 12, 4 to 8 p.m., at the Historic Civic Center.
The house the festival committee once worked from is open on a regular schedule. The Society posts docent tours of the Bradlee-McIntyre House on Wednesdays and Sundays from 1 to 4 p.m. On that schedule, the Sunday slot overlaps the festival's second day.
The 50th, Hour by Hour
The organizer describes the 2026 festival as more than 150 artists and hand-craft exhibitors selling jewelry, seasonal decor and original work, with festival food, beer, wine and music. Admission is free. The city's calendar lists more than 200 original artists and crafters. Either way, the festival is now held the weekend before Thanksgiving, and the organizer pitches it as a jump on holiday shopping. Vendors get in through a selection process the organizer calls "quasi-juried."
Saturday, Nov. 21: 9 a.m. to 5 p.m. The city calendar's event header and the organizer's vendor page both list a 5 p.m. close. A longer description on the city page says 4 p.m., so plan your browsing earlier in the day if timing matters.
Sunday, Nov. 22: 9 a.m. to 4 p.m.
Where: The Historic District. Last year's guest map put booths along W. Church Ave. and N. Ronald Reagan Blvd., with Wilma St., W. Warren Ave. and S. Milwee St. inside the layout. For setup, the 2026 vendor instructions send all exhibitor traffic in at Church Ave. and S. Milwee St. in a one-way flow. Expect that corner to be busy early Saturday morning.
Parking: The organizer says there is ample parking at SunRail and "at the hospital." The festival FAQ gives those as the SunRail lot at 149 E. Church Ave. and the former Orlando Health South Seminole Hospital at 555 W. SR 434. However, that FAQ still shows 2025 dates. The hospital site has changed since then. WESH reported that the full hospital closed on January 11, 2025. In April 2026, the Orlando Business Journal described the campus as a candidate for a possible mixed-use redevelopment. If you plan to park there, check with the city before you go. The SunRail lot is the safer default.
Pets: The FAQ says well-behaved pets are allowed but strongly encourages leaving them at home. That guidance is also on the page with last year's dates.
Papa Bees Made Its Own Move Up the Road
Longwood's longest-running restaurant story this fall also involves a move. Orlando Weekly reported that Papa Bees, open since 1986, is leaving its longtime home at 480 S. Ronald Reagan Blvd. for a larger space up the road at 190 S. Ronald Reagan Blvd. The new location was scheduled to open at 4:30 p.m. on Thursday, Oct. 29, and service at the old address was to end then.
The new space is the one Holy City Zoo BBQ left when it closed effective June 1, 2026, as Orlando Shine reported. Papa Bees itself started somewhere else. According to Orlando Weekly, the Burke brothers, Joe, Mike, Jerry and Kevin, opened it on Curry Ford Road and named it for their father, Bernard Burke, before it settled in Longwood. Some of the brothers had worked at the Anchor Bar in Buffalo, which inspired the sauce. The menu now has 22 house-made sauces, including the "Nuke," and the restaurant has long been a place for Buffalo Bills fans. Lorie Hamm is the current owner.
A 40-year-old wing house moved a short way up the same boulevard that runs through the festival. It is the same pattern as the two houses on Warren and Church, at a smaller scale.
The Rest of November, Built Around the Big Weekend
The city's Reiter Park calendar fills the Saturdays before and after the festival. In the Historic District, the Society's events pick up once the craft booths are gone.
- Every Saturday, Nov. 7, 14, 21 and 28: Farmers Market at Reiter Park, 311 Warren Ave., 9 a.m. to 1:30 p.m. On Nov. 21, it runs at the same time as the festival's first day.
- Saturday, Nov. 7: The rescheduled Longwood Luau at Reiter Park, 4 to 8 p.m., with live Hawaiian music, hula dancers, fire knife performers, Hawaiian food and drinks, and limbo and hula hoop games.
- Saturday, Nov. 14: Two events at once from 4 to 8 p.m. One is the city's Bites & Beats concert and food-truck battle at Reiter Park. The other is the Society's monthly car show at the Historic Civic Center on W. Church Ave.
- Nov. 21 and 22: The 50th Longwood Arts & Crafts Festival.
- Saturday, Nov. 28: Carols & Cocoa at the Bradlee-McIntyre House Museum and the Historic Civic Center, 3:30 to 6 p.m.
- Thursday, Dec. 3: The city's Holiday Concert & Tree Lighting at Reiter Park, 7 to 9 p.m.
- Friday, Dec. 11: Celebrate the Season, a holiday street party at Reiter Park with a tree-lighting ceremony and entertainment, 6 to 9 p.m.
For food during festival weekend, there are two nearby options. GoodWay Café at 111 W. Magnolia Ave. is a French plant-based café in the Historic District, which Orlando Weekly reviewed in April 2026. Nan & Pops Ice Cream Shop at 351 N. Ronald Reagan Blvd. posts Tuesday through Sunday hours. The Cottage Gift Shop inside the 1873 Inside-Outside House on W. Church Ave. rounds out the walk.
Longwood's Historic District was put together on purpose in the 1970s, and its best-known businesses keep picking up new addresses. If you own a rental near the district, or are thinking about renting one out, Evolve Property Group can tell you what it could earn in today's market. Get a Free Rental Analysis before the festival weekend arrives.
