"The vicinity surrounding the intersection of Ronald Reagan Boulevard and State Road 434 in Longwood is quickly becoming one of Central Florida's most diverse culinary pockets," Orlando Weekly wrote this April. The Longwood Arts & Crafts Festival returns to the Historic District for its 50th year on November 21 and 22. The booths will go up on the same streets as always. Around them, a lot has changed. The parking you'll use is on the grounds of a hospital that has closed, and some of the most interesting lunch options are at the Ronald Reagan and SR 434 corner that Orlando Weekly singled out.
The part that stays put
The festival is always held the weekend before Thanksgiving, on the streets of Longwood's historic district. For your GPS, the organizers give 175 W. Warren Ave. The organizers called the 2022 festival the 46th annual, so this year really is number 50.
Here's what the weekend looks like:
- Hours: Saturday, November 21, 9 a.m. to 5 p.m.; Sunday, November 22, 9 a.m. to 4 p.m.
- Admission: Free.
- Exhibitors: The festival's FAQ says more than 150 artists and crafters, 98% of them original artists. The City of Longwood's listing says more than 200.
- Beyond the booths: A free kids' zone, festival food, beer, wine and cocktails, and live entertainment on both days.
- Reputation: According to the organizers, the festival regularly makes Sunshine Artist Magazine's Top 200 Best Festivals in the USA.
Admission is free because of the vendors. Sponsors and a small number of retail businesses pay a higher booth fee, and the FAQ says that money helps cover costs. The site's own pitch is about getting a head start on holiday shopping, with handmade jewelry and seasonal decor among the draws.
The buildings around the booths have been there far longer than the festival. The Longwood Historic Society says Edward Warren Henck commissioned the Longwood Inn at 300 N. Ronald Reagan Blvd. in 1883. It was mostly finished in 1885 and completed in 1886. Christ Church at 151 W. Church Ave. dates to 1881, and the society calls it Seminole County's oldest continuously operating church. The society itself was founded in 1969 to save historic structures like these. So on festival weekend, you're shopping for handmade gifts on streets lined with 1880s buildings that people worked to keep standing.
The parking lot used to be a hospital
This is the biggest change at the edge of the festival. The FAQ lists two free lots:
- The former Orlando Health South Seminole Hospital, 555 W. SR 434
- The SunRail parking lot, 149 E. Church Ave.
Accessible parking is at Reiter Park, 331 W. Warren Ave., and the organizers say the event is fully accessible.
The word "former" is new. In 2025, the Orlando Business Journal reported that a new Orlando Health ER had opened as the Longwood hospital closed for good. The paper said the health system plans to redevelop the site after moving much of its services to Lake Mary. An earlier plan, covered by Florida Construction News, called for a freestanding emergency department and turning most of the campus into a 15-acre town center with apartments, retail and offices. Two existing medical office buildings would stay. FOX 35 also reported that the new ER would replace the hospital at the same address. That town center is still an announced plan. For now, the campus is where the festival's free parking is.
On pets, the organizers allow well-behaved dogs but strongly encourage you to leave them home. The streets get crowded, and the FAQ says even calm dogs can react unpredictably when strangers and other dogs are that close.
Lunch is a short walk from the booths
The festival will have its own food vendors, and there's more just past the booths. GoodWay Café, at 111 W. Magnolia Ave., is inside the Historic District, in the Victorian-style Magnolia Yoga & Wellness Center. It's a French plant-based café, and Orlando Weekly reviewed it in April 2026. The chef, Amandine Vibert, was born in Bordeaux and cooked in St. Tropez, on the Basque Coast and at EPCOT's France pavilion before coming to Longwood.
At the time of the April review, the menu included a gluten-free buckwheat galette bretonne for $12 and a crustless chickpea curry quiche for $11. Croissants come from Curious Cat Bakery in Tampa, and bread comes from local bakers including Olde Hearth. The café's details are at goodwaycafe.com.
Head toward Ronald Reagan Boulevard and SR 434 and there are more choices. The same Orlando Weekly review named these spots around that intersection:
- Guntur Kitchen, which the paper reviewed the week before
- Summer Breeze Roti Shop, serving Trinidadian food
- Cupid's, a California-style hot dog spot
- Taino's Puerto Rican Flavors
- Holy City Zoo BBQ, which was "soon-to-open" in April, so check that it's open before you plan around it
Farther up the boulevard, Mi Casa Kitchen at 2520 N. Ronald Reagan Blvd., Suite 148, serves Puerto Rican food. Its website says it was named Best Longwood Restaurant by Orlando Weekly in 2025.
So here's how it adds up. A festival in its 50th year now has a French plant-based café inside the district and Trinidadian, Puerto Rican and California-style spots around the Ronald Reagan and SR 434 corner. You could spend Saturday morning at the booths and still have a choice of lunch beyond the festival food stands.
Reiter Park Saturdays through festival weekend
Reiter Park is where most of the November lead-up happens, and its lot is also the festival's accessible parking. Here's what the City of Longwood has scheduled between this post and the festival:
| Date | Event | Time | Where |
|---|---|---|---|
| Saturday, October 31 | Farmers Market | 9 a.m. – 1:30 p.m. | Reiter Park |
| Saturday, November 7 | Longwood Luau, rescheduled | 4 – 8 p.m. | Reiter Park |
| Saturday, November 14 | Bites & Beats concert and food-truck battle | 4 – 8 p.m. | Reiter Park, 311 Warren Ave. |
| Saturday, November 14 | Downtown Longwood Cruise-in Car Show | 5 – 8 p.m. | Historic Longwood |
| November 21–22 | 50th Annual Longwood Arts & Crafts Festival | Sat. 9 a.m. – 5 p.m., Sun. 9 a.m. – 4 p.m. | Historic District |
The Luau is listed as rescheduled, so check the City of Longwood calendar that week. November 14 is the busiest night on the list. Bites & Beats runs at Reiter Park from 4 to 8, and the cruise-in starts in Historic Longwood at 5, so you can catch both. A week later, the festival takes over the same streets for its 50th weekend.
If you're walking the festival this year and wondering how downtown's changes, from the old hospital campus to the new restaurants, affect your own home, Diane Sterling is happy to talk it through. She's been working in Central Florida neighborhoods like Longwood for more than two decades. Let's Connect.
