On December 3 and 4, 1977, a group then called the Central Florida Society for Historic Preservation held a two-day fair in Longwood. It ran in the afternoons and had art vendors, food booths and music performers. The Society's own history calls it "a huge success!" Four years earlier, in 1973, two old houses had been moved to Longwood. One was the Bradlee-McIntyre House, brought over from Altamonte Springs. The other was the Inside-Outside House, built in 1873.
On November 21 and 22, the 50th annual Longwood Arts & Crafts Festival returns to the Historic Longwood District. If you live in Alaqua Lakes and go every year for holiday gifts, you have been shopping among buildings owned by the group the festival was started to fund.
The houses came first, then the festival
The Longwood Historic Society, the current name of the 1977 group, says it owns and maintains three buildings in the district from the 1870s and 1880s: the Historic Civic Center, the Inside-Outside House and the Bradlee-McIntyre House. Two of them came from somewhere else in 1973. The festival followed in 1977 as a fundraiser for the Society, and it stayed the Society's main fundraiser for about 40 years.
Forty years from an upstairs office
The work of running the festival happened in one of the Society's own houses. The Society's history of the festival puts it this way:
"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."
So for four decades, the festival committee planned the fair from a museum building on Warren Avenue, the same street the festival's GPS address uses.
That changed in 2017. The City of Longwood asked to take over running the show, and the Society agreed on the condition that it would keep receiving a royalty. With the planning off its plate, the Society started other events, including the Longwood Monster Dash 5K in 2018.
Today, the festival's website lists WTDI, Inc. as the event coordinator and says the site is separate from the City. According to the visitor FAQ, fees paid by sponsors and a limited number of retail businesses help cover costs so the public gets in free. The money now passes through the City and a coordinator instead of a volunteer committee. Under the 2017 agreement, a royalty still goes to the Society that owns the houses.
A walk through the district, one building at a time
Most visitors move through the festival booth by booth. You can also walk it by its buildings, which shows how much of the setting the Society has kept standing. Here are four stops, in roughly the order you'd come to them from the Warren Avenue side.
Bradlee-McIntyre House, 130 W. Warren Ave. Boston architect Nathaniel Bradlee designed it as a winter home. It was moved from Altamonte Springs to Longwood in 1973 and is now a museum that offers tours. It is also where the festival committee kept its office for 40 years.
Inside-Outside House, 141 W. Church Ave. Built in 1873 and moved to Longwood in 1973, it now houses the Cottage Gift Shop. The Society says the Redditt family has run the shop since 1995. The festival sells handmade gifts for one weekend, and this gift shop has been in the district for three decades.
The Historic Civic Center. It has been a community gathering place since 1880 and is now the Historic Society's clubhouse. The building used by 1880s Longwood is now used by the group that started the festival.
The old Longwood Hotel site, 300 N. CR 427. Longwood's first hotel opened in 1883 and burned in the 1890s. A second hotel at 300 N. CR 427 went by several names over the years, including Longwood Hotel, St. George and Orange and Black. The Society's trail history says it was also called the Longwood Village Inn and was turned into offices in the mid-1980s. This stop is about the town's past more than anything you can visit inside, and the Society's Longwood Historical Trail covers it in more detail.
Three of these four buildings belong to the Society that has received the festival's royalty since 2017.
The 50th weekend in practical terms
The festival is held the weekend before Thanksgiving. Here are the details posted for 2026:
- Dates and hours: Saturday, November 21, 9 a.m. to 5 p.m.; Sunday, November 22, 9 a.m. to 4 p.m. These are the organizer's hours. The City of Longwood's event listing gives the same times in its main entry.
- Admission: Free. The event is outdoors and goes on rain or shine, with live entertainment.
- Exhibitors: The festival website promises more than 150 artists and craft exhibitors selling handmade items, fine jewelry and seasonal decor. The City's listing says more than 200. Both sources expect a full street.
- Food and drink: Festival food, beer, wine and music, according to the organizer.
- Where to point your GPS: The FAQ gives 175 W. Warren Ave.
- Parking: The festival homepage says there is plenty of parking at SunRail and at the hospital. The FAQ gives the details: free parking at the SunRail lot, 149 E. Church Ave., and at the former Orlando Health South Seminole Hospital.
- Dogs: The FAQ says well-behaved pets are allowed but strongly encourages leaving dogs at home because the streets can get crowded.
If you park at the SunRail lot at 149 E. Church Ave., the Inside-Outside House at 141 W. Church Ave. is on the same street, to the west.
The district stays busy into December
The festival kicks off a full month in Longwood. The City runs several holiday events in December, and with the festival they make up a season worth putting on the calendar now:
- Holiday Concert & Tree Lighting: Thursday, December 3, 7 to 9 p.m., Reiter Park, 311 Warren Ave.
- 12th annual Christmas Parade: Saturday, December 5, 3 to 5 p.m., on Ronald Reagan Boulevard north of SR 434.
- Celebrate the Season: Friday, December 11, 6 to 9 p.m., Reiter Park.
Reiter Park's address is on Warren Avenue, the same street as the Bradlee-McIntyre House, so the City's December events stay on the same street the festival uses in November.
If you're driving in this season, FDOT has a project at the intersection of SR 434 and CR 427, also known as Ronald Reagan Boulevard. The project adds dual left-turn lanes, an eastbound right-turn lane, bike lanes, drainage, sidewalk and signal work. FDOT's project page lists a fall 2026 start and estimated completion in summer 2028, and showed no lane closures at the time it was posted. Check that page before parade day, when Ronald Reagan Boulevard is also the parade route.
The first festival in 1977 ran only in the afternoons. The 50th starts at 9 a.m. on Saturday and runs from the SunRail lot on Church Avenue to the museum on Warren Avenue.
If walking among Longwood's 1870s houses gets you wondering what your own home is worth this season, Holt Real Estate can give you an appraisal-informed answer. Get a Free Home Valuation, and enjoy the 50th.
