On a regular weekday, the stretch of North Ronald Reagan Boulevard between Warren and Church Avenues is just a few quiet historic blocks you drive through on the way somewhere else. On the weekend before Thanksgiving it fills with artists' tents. For the 50th time this November, the Longwood Arts & Crafts Festival takes over the Historic District on Saturday and Sunday, November 21 and 22, 2026.
Ronald Reagan Boulevard ties Longwood's holiday season together. It carries booth rows during the festival and a Christmas parade two weeks later. It holds two of Longwood's oldest buildings and one of its newer taproom addresses. If you plan the festival weekend around this one street, the rest of the season around it makes sense too.
Fifty Years on the Weekend Before Thanksgiving
The organizers' visitor FAQ says the festival "always runs the weekend before Thanksgiving," which is why it lands on November 21 and 22 this year. The official festival site promises more than 150 artists and handcraft exhibitors selling jewelry, seasonal decor and other handmade pieces. It also lists festival food, beer, wine and live music. Admission is free.
The visitor FAQ explains how it stays free. About 98% of exhibitors are original artists. Sponsors and a limited number of retail businesses pay a higher booth fee, and that money helps cover costs so there's no gate charge. The FAQ also lists a free kid zone, cocktails and entertainment on both days. The festival regularly appears in Sunshine Artist Magazine's list of the 200 best festivals in the country.
On hours, the City of Longwood's event listing gives Saturday as 9 a.m. to 5 p.m. and Sunday as 9 a.m. to 4 p.m. Another line on the same page says Saturday closes at 4. If you're aiming for a late Saturday visit, check the page again closer to the weekend. The City's listing also says more than 200 artists and crafters, compared with the festival site's 150-plus, so plan on a big crowd of booths either way.
Where the Tents Go and Where the Cars Go
The 2026 map and exhibitor list hadn't been posted yet as of mid-October. Last year's guest map set up booth rows along W. Church Avenue, N. Ronald Reagan Boulevard, Wilma Street, W. Warren Avenue and S. Milwee Street. If organizers keep a similar layout, Ronald Reagan Boulevard will again be the line between the Church Avenue rows and the Warren Avenue rows. For GPS, organizers use 175 W. Warren Ave.
The FAQ lists two free parking areas:
- SunRail lot, 149 E. Church Ave. This is the closer lot, on the east side of the district.
- The former Orlando Health South Seminole Hospital, 555 W SR 434. This is a large lot on the State Road 434 side.
- Accessible parking is in Reiter Park, which the FAQ lists at 331 W. Warren Ave. Organizers describe the event as fully accessible.
The word "former" there reflects a real change in Longwood. WFTV reported in September 2022 that Orlando Health planned to close South Seminole Hospital and reimagine the campus. According to WESH, the hospital closed on January 11, 2025. Patients were moved that morning to Orlando Health's new hospital in Lake Mary, and an emergency department was planned for the Longwood campus. Orlando Health's own page lists the Lake Mary hospital at 380 Rinehart Road. Parts of the old campus are still active, so park where festival signs direct you.
Organizers allow well-behaved dogs but put their advice plainly:
"The streets can get crowded, and even the gentlest dogs may be uncomfortable and react unpredictably to strangers in close proximity as well as other dogs."
That comes from the festival FAQ, which strongly encourages guests to leave pets at home.
A Walk That Follows the Boulevard
The booths are the main draw. The buildings behind them are what make the weekend a Longwood outing. The Longwood Historic Society says it owns and maintains three district buildings dating to the 1870s and 1880s. Here is one route that starts at the historic end and finishes at the taprooms:
- Bradlee-McIntyre House Museum, 130 W. Warren Ave. Nathaniel Bradlee built it as a winter cottage in Altamonte Springs in 1885, and it was moved to Longwood in 1973. The Society's tour page lists regular tours on Wednesdays and Sundays from 1 to 4 p.m. Festival Sunday falls on November 22, so call ahead to see whether the house is open that afternoon.
- Inside-Outside House, 141 W. Church Ave. This mail-order home was put together in Altamonte Springs in 1873 and moved to its current spot in 1973. Today it holds the Cottage Gift Shop.
- The Longwood Inn building, 300 N. Ronald Reagan Blvd. The former Longwood Village Inn was renovated into office space after it sold in 1983, according to the Historic Society's building history. You can admire the exterior, but it isn't a hotel anymore.
- 351 N. Ronald Reagan Blvd. A short walk north brings you to Alestone Brewing Co. in Suite 1055, which serves beer, pizza and sandwiches. Its live music calendar ran into this year, including a show on March 6, 2026. Nan & Pops Ice Cream Shop's website lists the same building at Suite 1005. Check its posted hours before you walk over with kids.
- Hourglass Brewing, 480 S. Ronald Reagan Blvd. South of the district, the Hourglass taproom mentions food trucks and art shows on its site. That makes it a good stop after the festival if you'd rather drive a few minutes than wait in a line on Warren Avenue.
Stop one and stop five sit on the same street, and every stop in between is on or just off it.
The Boulevard Stays Busy Into December
Bites & Beats kicks things off a week before the festival, and three more events follow in December. The City calendar fills the weeks around it, mostly at Reiter Park and on Ronald Reagan Boulevard:
| Date | Event | Where | Hours |
|---|---|---|---|
| Sat., Nov. 14 | Bites & Beats, a concert and food truck battle | Reiter Park | 4–8 p.m. |
| Sat.–Sun., Nov. 21–22 | 50th Longwood Arts & Crafts Festival | Historic District | 9 a.m. start both days |
| Thu., Dec. 3 | Holiday Concert & Tree Lighting | Reiter Park | 7–9 p.m. |
| Sat., Dec. 5 | Christmas Parade | Ronald Reagan Blvd. north of SR 434 | 3–5 p.m. |
| Fri., Dec. 11 | Celebrate the Season | Reiter Park | 6–9 p.m. |
Two of these are especially good for families. The City's listing for Celebrate the Season includes a tree lighting, live performances, a snow maze, rides, food, shopping and a laser-light finale. Bites & Beats a week before the festival is the lower-key warm-up.
The Historic Society added its own events to this stretch last year. Its 2025 Carols & Cocoa announcement described ticketed walking tours inside six historic buildings on November 29, 2025. That was followed by a free public tree lighting and caroling on Ronald Reagan Boulevard between Warren and Church Avenues. The Society also offered free Bradlee-McIntyre House tours from Thanksgiving through New Year's. If last year's caroling night is on your list, check the Society's news page for 2026 dates.
Change along State Road 434 is moving more slowly. The City's development update map, dated September 11, 2026, shows Fire Station #15 next to Reiter Park still under review with revised architectural plans. That means this season's park events should happen around the same grounds you already know. The same map lists Jack in the Box as open at 815 W. State Road 434 in the former Wendy's building, and an Aldi under construction in part of the old Winn-Dixie space.
For the full run, here's the order: Bites & Beats at Reiter Park on November 14, the festival on November 21 and 22, the tree lighting on December 3, the parade up Ronald Reagan Boulevard on December 5, and Celebrate the Season on December 11.
If you're picking up handmade gifts on Warren Avenue this November and wondering how your own Longwood home fits into your plans for next year, I'd love to talk it through with you over coffee near the Historic District. Rebecca Simms is happy to answer questions with no pressure. Schedule a Free Consultation.
