September 2026 events in Monterey

Taste of Crossville

Downtown Crossville hosts its annual local-food showcase from 6 to 8 PM. Restaurants, food trucks, caterers, and other local food businesses gather downtown for an evening centered on Cumberland County flavors.

Arts

First Friday Arts - September

Art Round Tennessee's monthly First Friday event brings the arts to Cookeville's Historic Westside. Stroll from gallery to gallery, meet local artists, shop original work, and enjoy live music at stops including Edison Hills, Glass Tangerine, Plenty Bookshop, and more. Suggested $5 donation.

Concert

Muddy Roots Music Festival

Muddy Roots is an internationally recognized three-day camping music festival held near Cookeville every Labor Day weekend, bringing together roots, folk, country, and Americana acts from around the world. A passionate, devoted following draws attendees from across the country to the Upper Cumberland.

Sports

TTU Golden Eagles Football, Home Opener

Tennessee Tech kicks off the 2026 football season at Tucker Stadium. Come out and cheer on the Golden Eagles in their first home game of the year.

Concert

Bryan Symphony Orchestra at Dogwood Park

The Bryan Symphony Orchestra presents its annual free outdoor community concert at 7 PM. Professional musicians from across the region, including Tennessee Tech faculty and select students, perform under the stars at Dogwood Park.

Concert

Big Band Sound Orchestra - September

A free evening of swing and big band standards from the Big Band Sound Orchestra at Dogwood Park, presented by the city Leisure Services and Cultural Arts Division. Music begins at 7:30 PM. Bring a lawn chair and enjoy the show.

Sports

Beginner Pickleball Clinics

Learn pickleball fundamentals in morning and evening clinics at Cane Creek Gym and the outdoor courts, weather permitting. Sessions run Tuesdays and Saturdays from September 8 through October 3, with registration required.

Fall FunFest

Cookeville's beloved Main Street festival returns for its 29th year with two days of live music, artisan vendors, crafts, food, and family activities in the heart of downtown. One of the Upper Cumberland's most popular fall traditions, drawing thousands to the square each September.

Warren County Agricultural & Livestock Fair

McMinnville's community fair returns with agricultural and livestock exhibits, pageants, local bands, grandstand entertainment, food vendors, and a carnival. The fair runs September 11 through 19 and remains one of Tennessee's free county fairs.

Crossville's 125th Birthday Celebration

Crossville celebrates 125 years with a downtown community gathering from 10 AM to 5 PM. The anniversary event takes over Main Street for a full Saturday of birthday festivities.

Downtown History Hike

Explore downtown Cookeville's history with a guided "hike" between the Cookeville Depot Museum and the Cookeville History Museum on Broad Street. Held the second Saturday of each month, April through October, from 10:30 AM to 2:30 PM. Free and open to all ages.

Dogapalooza

A free dog-friendly festival at the Cane Creek Dog Park featuring dog-related vendors, rescues, and nonprofits, plus demonstrations and activities for pups and their people. Bring your leashed, friendly dog and enjoy a day in the park.

5th Annual Bacon Festival

Downtown Smithville fills with bacon-inspired food, local vendors, and community fun from 10 AM to 3 PM. Admission and parking are free.

TN Serves: Clean Up the Caney Fork

Volunteer with Rock Island State Park from 10 AM to noon to remove litter along the Caney Fork River Gorge between Twin Falls and Great Falls. Participants help care for one of the Upper Cumberland's signature waterways.

Cemetery Walk

A guided evening walk through the historic Cookeville City Cemetery where costumed interpreters portray notable local figures and share their stories at the grave sites. A memorable look at Cookeville's past. Registration required.

National Public Lands Day Hike

Join a Rock Island State Park ranger from 10 AM to 1 PM for a 1.95-mile hike through the park's upland oak forest. The ranger-led outing may cover park history, native plants and wildlife, and other points of interest along the route.

Arts

5th Annual Smithville Art Walk

Downtown Smithville celebrates local art, live music, and community from 3 to 8 PM. The walk brings artists and visitors together in the heart of town for an early-fall Saturday.

Rosenwald Schools Exhibit

The Cookeville History Museum presents a rotating exhibit about Rosenwald schools from September 28 through November 20. Visit free during regular museum hours, Tuesday through Saturday from 10 AM to 4 PM.