While July 4 has passed, America’s semiquincentennial year is still going strong – including an exciting lineup of festivals and events for September. Here’s a list of 10 worth checking out if you’re nearby, or if you’re looking for an impromptu trip as summer slides into fall.
Chicago Jazz Festival — Chicago, Illinois
September 3–6, 2026
The oldest of Chicago’s free lakefront music festivals, this four-day event fills the Jay Pritzker Pavilion at Millennium Park with everything from classic to experimental jazz. All performances are free and open to the public, with programming also running at the Chicago Cultural Center.
Lodging is available downtown near Millennium Park if walkability matters — the venue sits right off Michigan Avenue, accessible by the CTA Red or Blue Line. Bring a blanket or chair for the Great Lawn. Outside alcohol isn’t permitted, but food and non-alcoholic drinks are permitted. The full lineup includes vocalist Dee Dee Bridgewater and pianist Bill Charlap on opening night.
Fiesta de Santa Fe — Santa Fe, New Mexico
September 5–13, 2026
Now in its 314th year (yes, really!), Fiesta de Santa Fe is one of the longest continuously running public celebrations in the country. The nine-day event opens with the burning of Zozobra — a towering 50-foot-tall marionette effigy that symbolizes the collective anxiety, worries, and regrets of attendees — on September 4.
That highlight is followed by processions, mariachi performances, and events centered on the historic Santa Fe Plaza. Because the whole event unfolds within walking distance of downtown adobe architecture, it’s an easy one to experience entirely on foot.
Great Reno Balloon Race — Reno, Nevada
September 10–13, 2026
Now in its 45th year and expanded to four days for 2026, this is the largest free hot-air balloon event in the world. Balloons launch at dawn from Rancho San Rafael Regional Park, so plan for an early start — gates typically open well before sunrise for the best viewing. Admission is free, and terrain is flat and easy to navigate. Reno hotels within a short drive of the park fill up for this weekend, so book ahead if you want to avoid a long morning commute.
Kentucky Bourbon Festival — Bardstown, Kentucky
September 10–13, 2026
Bardstown calls itself the Bourbon Capital of the World, and this festival — celebrating its 35th anniversary in 2026 — is the reason why. The event includes tastings from distilleries across the region, educational sessions with master distillers, and the chance to buy limited releases not available elsewhere.
Tickets have sold out four years running, so this is not a buy-at-the-gate event; plan to purchase in advance through the official festival site. If you miss out on tickets this year, don’t worry — expect another exciting event next year as well. Bardstown’s downtown is compact and walkable, with lodging options ranging from historic inns to chain hotels.
Feast of San Gennaro — New York, New York
September 17–27, 2026
This 11-day street festival in New York’s Little Italy neighborhood marks its 100th anniversary in 2026 — a genuine milestone for one of the city’s oldest continuous cultural celebrations. Mulberry Street closes to traffic, instead filling with food vendors, live music, and religious processions honoring the festival’s patron saint.
The neighborhood is flat and walkable, with subway access via the 6 train to Spring Street or the B/D to Grand Street. Because it runs closer to two weeks than a single weekend, this festival is easy to work into a broader New York trip.
Savannah Jazz Festival — Savannah, Georgia
September 18–20, 2026
Savannah’s free jazz festival culminates in a three-day run at historic Forsyth Park, with additional performances at venues around the city earlier in the week. The setting under Forsyth Park’s live oaks is relaxed rather than crowded. Bring a blanket and plan to stay a while.
The festival sits within walking distance of Savannah’s historic squares, making it easy to combine with a day of walking tours. If you want a second stop nearby, Fort Pulaski National Monument just outside the city offers free admission on September 17 in honor of Constitution Day.
Custer State Park Buffalo Roundup — Custer State Park, South Dakota
September 25, 2026
Once a year, cowboys and cowgirls on horseback drive roughly 1,300 free-roaming bison about five miles into corrals for sorting and vaccinating — a genuine piece of Old West tradition come to life.
As of 2026, gates open at 6:15 a.m., with the roundup beginning at 9:30 a.m. Admission is free and the park entrance fee is waived that day, but there’s no bleacher seating — you'll be standing or sitting in an open field for several hours, so dress in layers and plan accordingly.
Lodging in Custer and the in-park lodges sells out well in advance of this specific weekend. The accompanying Buffalo Roundup Arts Festival also runs September 24–26 at the State Game Lodge grounds, with more than 150 vendors.
Longs Peak Scottish-Irish Highland Festival — Estes Park, Colorado
September 11–13, 2026
Known locally as ScotFest, this three-day celebration marks its 50th anniversary in 2026 with pipe bands, Highland dancing, athletic competitions, and a parade through downtown Estes Park. The festival grounds are at the Estes Park Fairgrounds and Event Center, roughly two miles from Rocky Mountain National Park hiking access — worth combining with a park visit if you’re making the trip. Estes Park lodging fills up fast for this weekend given the overlap with fall visitation to the national park, so book early.
Pensacola Seafood Festival — Pensacola, Florida
September 25–27, 2026
Downtown Pensacola’s historic Seville Square, Fountain Park, and Bartram Park fill with Gulf seafood vendors, live music, and arts and crafts for this free, three-day event. The grounds are walkable and centered in the historic Seville neighborhood, making it easy to pair with a stroll through downtown Pensacola. One honest caveat: late September still falls within Atlantic hurricane season, so it’s worth keeping a flexible eye on the forecast in the weeks leading up to the trip rather than assuming settled fall weather.
Common Ground Country Fair — Unity, Maine
September 25–27, 2026
This celebration of rural living marks its 50th anniversary in 2026, drawing more than a thousand exhibitors to 250 acres of Maine farmland. Expect sheepdog demonstrations, draft horse and oxen pulling, traditional craft vendors, and food courts serving nothing but organic fare.
The fairgrounds are open Friday and Saturday from 9 a.m. to 6 p.m. and Sunday from 9 a.m. to 5 p.m. in Unity — about 2.5 hours north of Portland, so plan lodging in a nearby town like Waterville or Belfast rather than expecting options right at the fairgrounds. Advance tickets are on sale now and are required even for free admission categories, so reserve ahead rather than assuming walk-up entry.
Is there a can’t-miss September festival near your town that didn’t make our list? Tell us about it in the comments.
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