At 6 p.m. on Friday, October 2, the Eastern Shore Art Center at 401 Oak Street opens for First Friday. Trio Con Brio is playing, the Eastern Shore Camera Club's 16th Annual Photography Exhibit is on the walls, and an ArtSquared auction closes at 7. Over at Page & Palette, 32 South Section Street, local author Jo Taylor has been signing "Mimi and Maurice" since 5:30. Both events start the season. Neither one needs a car.
The same pattern holds for the next seven weeks. Line up the calendars from the art center, the library, Live at Five, the Baldwin Humane Society and the city, and almost every date lands at a small set of downtown addresses. The exceptions are Founders Day on the bluff and the painters on the pier, and both of those head toward the water.
The addresses that carry the season
Here is where the fall happens, by street:
- Fairhope Avenue. Halstead Amphitheater sits on Coastal Alabama Community College's Fairhope campus at 440 Fairhope Avenue. Fairhope Public Library and its Giddens Conference Center are at 501 Fairhope Avenue.
- Section Street. Page & Palette is at 32 South Section Street. Fairhope United Methodist Church is at 155 S. Section Street.
- Oak Street. The Eastern Shore Art Center is at 401 Oak Street.
- Bancroft and Magnolia. The Thursday farmers market runs 2 to 6 p.m. at this corner, which the city describes as behind the public library.
Each address hosts more than one event this fall, so the calendar below is organized by those addresses.
October starts on the bluff and moves inland
On Sunday, October 4, the Baldwin Pops play their 28th annual Founders Day Concert at Henry George Bluff Park from 6 to 8 p.m. The city invites people to bring a picnic, a blanket or a lawn chair. It is the only October event on the calendar set on the bay.
Everything after that heads back up the hill. On Wednesday, October 14, Alabama author Matt Kessler comes to Page & Palette at 6 p.m. to sign and discuss "The Wiregrass: A Tale of Murder and Retribution in the Deep South," in conversation with local journalist Cori Yonge.
On Saturday, October 17, the South Alabama British Car Club holds "The Ghosts We Drive" at Fairhope United Methodist Church, farther down Section Street from the bookstore. Registration runs 9 to 11:30 a.m. and the show runs 11:30 a.m. to 3:30 p.m. If you plan to go, check admission directly with the club first, since a state tourism listing for the festival calls it free in one place and charges admission in another.
The church comes up again later in the month. Live at Five says Fairhope United Methodist, at Morphy Avenue and Bancroft Street, typically offers paid parking on concert nights.
Halloween week, day by day
The busiest stretch of the fall falls between October 23 and October 31. Every stop sits within the same few downtown streets:
- Friday, October 23. Sammy Kershaw plays Live at Five at Halstead Amphitheater. This is the date on the series' show page.
- Saturday, October 24, 10 a.m. to noon. Downtown Fairhope Trick-or-Treat. Kids collect treats from participating merchants, and there's a Halloween photo spot at the Welcome Center.
- Saturday and Sunday, October 24 and 25. Witches Ride riders pick up wristbands and sign liability waivers at Up Tail Resale in Fairhope.
- Thursday, October 29, 5:45 to 9 p.m. The Fairhope Witches Ride rolls through downtown and ends with the Witches Ball at Halstead Amphitheater.
- Saturday, October 31. Fairhope Public Library's October calendar lists a program with Gabe Gold-Vukson, director of the Fairhope Museum of History. The calendar entry doesn't give a time, so check with the library before you go.
October 29 is a Thursday. The farmers market's listed hours at Bancroft and Magnolia run until 6 p.m., so its last fifteen minutes overlap with the start of the ride.
What the Witches Ride allows
The Baldwin Humane Society's ticket page describes several hundred witches and warlocks riding through downtown, followed by a ball with music from 12 South Band and food trucks on site. Anyone can watch the ride from the street. The ball is for ages 21 and up, and every ride ticket includes admission to it.
The rules are short, and they're written plainly:
*no e-bikes* *no golf carts* *no walking witches* no pets
Riders buy single tickets only, because each rider needs their own for liability reasons. The ball is BYOB, coolers are welcome and you can bring a chair, but personal tents and tables aren't allowed. If the weather turns, the ride is canceled and the ball moves to Oak Hollow Farm, the one time this season an event leaves downtown entirely. Organizers call it a charity event run by a small group of women for local animals in need, and there are no refunds.
November sends the easels to the pier
Plein Air Fairhope runs Monday, November 2, through Saturday, November 7. Sixty painters set up with portable easels, chairs and umbrellas from sunrise to sunset, around town and on the bayfront pier. This is the second time this fall the calendar goes down to the water. The pier the painters will set up on is newly improved. In March, the city reported that nearly $10 million in waterfront work was finished, including bulkhead and seawall repairs, accessible pedestrian access, pier enhancements and upgrades to the fountain and facilities.
The paintings then go back up the hill. Work from the paint-out is shown and sold at the Eastern Shore Art Center, and Wet Room paintings are on display during event week. The reception falls on the November 6 First Friday Art Walk, and the exhibit stays up through December 19. The art center's November Art Walk page wasn't live yet when we checked. Its earlier 2026 Art Walks ran 6 to 8 p.m.
The paint-out is popular with the painters themselves. Registration opened August 10 on a first-come basis with a cap of 60, and the art center says last year's spots were gone in a few days.
One room at 501 Fairhope Avenue, three uses in four days
The library's November calendar shows the season packing into a single building. On Thursday, November 12, the Friends of the Library book sale runs 9 a.m. to 3 p.m. in the Giddens Conference Center, and the same calendar lists Fairhope Film Festival setup in Giddens from 8 a.m. to 8 p.m. that day. From November 13 through 15, the library lists "Fairhope Film Festival – Giddens" each day, 8 a.m. to 8 p.m.
The 14th Annual Fairhope Film Festival runs November 12 to 15. When we checked, the festival's own site was only collecting sign-ups for updates and hadn't posted a 2026 lineup or ticket details. Giddens is the only 2026 screening room we could confirm. Last year's festival used several venues around town, but those shouldn't be read as this year's list until the festival announces it.
Robert Earl Keen closes the season at Halstead
On Friday, November 20, Robert Earl Keen plays Live at Five, the last fall show listed before the 2nd Annual Memorial Jam on December 18. A few of the series' rules are worth knowing before you buy. At national touring acts, everyone needs a ticket regardless of age. At local and regional shows, children five and under get in free. Tickets are nonrefundable unless the show is canceled. The series points concertgoers to street parking around downtown and the church lot at Morphy and Bancroft.
Getting downtown without the car
There may soon be a new way to ride in from the south. On September 30, Gulf Coast Media reported that the Eastern Shore Trail's 1.84-mile extension from the Fish River bridge through Pleasant View Lane was about 80% complete. It's an 8-foot asphalt path along U.S. 98, and county officials expect to finish it by November. Taylor Bufkin said the segment closes a gap in the network and puts more space between trail users and traffic. County officials are describing that date as an expectation, not a promise, so the bike may have to wait until Plein Air week or the film festival.
Two things that might seem like they belong on this list don't. Fairhope Brewing held its Oktoberfest on September 12. The Arts and Crafts Festival is a March event, and the city lists the next one for March 19 to 21, 2027.
Living within walking distance of Halstead, the art center and the Section Street shops is part of what a downtown Fairhope home is worth, and it rarely shows up on a listing sheet. If you're curious how that walkability factors into your home's value this fall, Top Tier Team will look at it with you the way we would for family. Get your free home valuation.
