Porchfest Annapolis Trades June Heat for October in Murray Hill

Porchfest Annapolis is coming back for its second year, and this time the free porch-to-porch music festival is trading its original June date for a crisper October afternoon in the Murray Hill neighborhood. The event runs from 11 a.m. to 3 p.m. on October 24, with a rain date set for October 25, and organizers say more than 25 local musical acts will perform on eight to ten front porches and stoops turned into makeshift stages.

The move to Murray Hill and the switch from summer to fall both trace back to feedback from the musicians themselves, according to Eye On Annapolis. Lead artist Kaitlyn McQuaid said the event was moved from June to a cooler season at performers' request, a shift organizers hope will make the day more comfortable for both musicians and the crowds walking house to house through the neighborhood's tree-lined streets.

Murray Hill itself brings some history to the occasion. The neighborhood, just west of downtown Annapolis along Spa Creek, was carved out as a residential subdivision in 1890 from the old Acton Hall plantation, and it's known today for its walkable streets and mix of post-Victorian, bungalow, and revival-style homes, according to Annapolis Home Magazine.

From Germantown-Homewood to a Bigger Bill

Porchfest Annapolis followed its inaugural year in the Germantown-Homewood neighborhood, where the debut event in June 2025 drew roughly 40 acts performing on private porches and community stages, including the Artfarm stage at The Hippie Mansion. McQuaid said last year's inaugural Porchfest in Germantown-Homewood was an amazing success, and the 2026 lineup builds on that momentum with a slate spanning classical, jazz, Irish, blues, American roots, original songs, acoustic pop, and rock. Acts will play 40-minute acoustic sets throughout the afternoon as visitors wander from porch to porch.

The scheduled performers mix hometown star power with rising and institutional talent. Jimi Haha, born Jimi Davies and best known as the frontman of Annapolis alternative rock band Jimmie's Chicken Shack — which signed with Elton John's Rocket Records in 1996 and scored national hits with “High” and “Do Right,” per Wikipedia — is set to perform, alongside singer-songwriter Doug Segree, whose music has appeared on ABC's Cougar Town and TNT's Rizzoli & Isles according to his own site. Also on the bill are Madisun Bailey and The Befuddlers, along with members of the Annapolis Symphony Orchestra and Annapolis Symphony Academy.

Grants and Volunteers Keep the Porches Running

Pulling off a free, all-ages festival across someone's front yard takes institutional backing. The Arts Council of Anne Arundel County has sponsored Porchfest Annapolis; the council distributes project-specific mini-grants of up to $2,500 with a 1:1 matching requirement to support local arts initiatives, per The BayNet. The Annapolis Musicians Fund for Musicians has also sponsored the event, alongside several other business sponsors, and the festival is still seeking additional local sponsors ahead of October.

Organizers are also looking for volunteers to serve as porch managers, who help performers find their assigned porches, understand access, and stay on schedule during two-hour shifts. McQuaid said volunteers can still enjoy the festival and visit other porches before or after their shift, making the ask a low-lift way to pitch in. The full lineup, schedule, porch map, and sponsor list will be posted on the Porchfest Annapolis website as details are finalized.

Part of a Bigger Local — and National — Trend

Annapolis has been leaning into open-air, non-traditional performance formats this year, from Chronic Sailing's floating Tunesday concerts on Back Creek, where audiences paddle up in kayaks and small boats, to the Annapolis Symphony Orchestra's free outdoor Pops in the Park shows marking its 65th season. Porchfest itself is a local branch of a much larger movement: the format began in 2007 in Ithaca, New York, created by neighbors Gretchen Hildreth and Lesley Greene, and has since spread to more than 250 communities across North America, according to Streetsblog USA. The Mid-Atlantic has embraced the idea too, with DC's own porch-hopping crawl pairing neighborhood performances with embassy open houses earlier this year.

For Annapolis, the appeal remains simple: free live music, open to the public, delivered on a human scale as neighbors open their porches to musicians and strangers alike. With a rain date already locked in for October 25, organizers appear confident the second Porchfest Annapolis will land, whatever the weather.