Autumn Glory Festival Car Show Mountain Top Cruisers - 9 am – 2 pm, Downtown Oakland. Biggest car show in Garrett County. Antique, Street Rod, Classic Car, Truck, Motorcycle & Tractor Show. Registration fee $20 includes t-shirt and dash plaque for the first 300. Food and raffle tickets. Oakland businesses will be open. Free for spectators. 301.334.4303 or 301.616.1358

The Town of Oakland and the Greater Oakland Business Association are proud to present the 59th Annual Autumn Glory Grand Feature Parade, taking place on Saturday, October 10, 2026 at 1:00 p.m. in downtown Oakland.

Celebrate the beauty of the fall foliage season at one of Garrett County’s most beloved traditions—the Autumn Glory Festival Grand Feature Parade. This signature event showcases vibrant marching bands, creative floats, and community groups, drawing visitors from across the region for an unforgettable afternoon filled with music, color, and hometown pride.

We are proud to welcome back First United Bank & Trust as the title sponsor of the 59th Annual Autumn Glory Grand Feature Parade, whose continued support helps make this cherished community celebration possible.

This year the event will be held on October 9th, 2026 at Southern Garrett High School in Oakland, Maryland. Joining us as master of ceremonies again this year is husband and wife team, Steve and Katie Smith, from the Steve Smith Band! At the end of the contests, we welcome all contestants to return to the stage for a Jam Session with Steve!

Applications must be received by Saturday, September 19th to be printed in the event program. Applicants may register at the door the night of the competition, up until 5:30pm.

The competition begins at 6:00 pm. Check-in and registration for participants is from 5:00-5:30pm. The doors open for spectators at 5pm. Registration forms may be mailed to Tracy Park, 15 S. Third Street, Oakland, Maryland or emailed to [email protected].

Please make sure to review the updated contest rules. This year we will have a combination of cash payouts and certificates. Cash payouts will be mailed out the week following the events completion.

The Maryland State Banjo, Fiddle, & Mandolin Championships have been an Autumn Glory tradition and a great family fun event for many years. Please feel free to share any of this information with family and friends. We welcome all participants and spectators. We hope to see you there.

Celebrate Fall at Fall Fest in Downtown Oakland!

Join us for Fall Fest on Friday, October 9, 2026, from 11 AM–4 PM on Second Street in downtown Oakland.

Enjoy games, prizes, and fun for everyone! Bring your family and friends and celebrate the season while you’re in town for Autumn Glory.

We look forward to seeing you downtown!

Autumn Glory Firemen’s Parade Set for October 8

Join the Oakland Volunteer Fire Department as it celebrates 132 years of service with the Annual Autumn Glory Festival Firemen’s Parade on Thursday, October 8, 2026, in Oakland, Maryland!

The parade begins promptly at 7:00 p.m. Come enjoy an evening celebrating the fire companies and rescue squads that serve our communities.

Information for Participating Departments

Parade units will begin assembling at 5:00 p.m. at Walmart, approximately one mile north of Oakland on Garrett Highway. Participating companies should arrive between 5:00 and 6:30 p.m. Units will enter the lineup in the order they arrive.

Judging will take place from 5:00 to 6:45 p.m. before the parade. Units must be judged to qualify for an award, and each company may enter only one unit per category.

Award Categories

• Best Appearing Firefighting Apparatus — 1,000 GPM and Above

• Best Appearing Firefighting Apparatus — 750 GPM and Below, including Engine/Mini Pumper

• Best Appearing Brush Truck

• Best Appearing Ambulance/Medic Unit

• Best Appearing Rescue Engine, Rescue, or Equipment Truck

• Best Appearing Tanker/Pumper Tanker

• Best Appearing Aerial Apparatus

• Best Appearing Specialized Unit — Command Unit, EMS Chase Unit, Boat, Fire/EMS Float, Chief’s Car, Air/Light Unit, or Utility Vehicle

• Best Appearing Antique Apparatus — 2001 or Older

• Best Appearing Fire Department — Two or More Units

• Judges’ Choice

• Longest Distance Traveled — Maryland

• Longest Distance Traveled — Out of State

For everyone’s safety, candy and other articles may not be thrown along the parade route.

Awards and Food Following the Parade

An awards ceremony for participating departments will take place immediately after the parade at the Oakland Volunteer Fire Department. Food vendors will also be available in the parking lot adjacent to the station for everyone to enjoy.

Departments staying for the awards are encouraged to park their units along both sides of Second Street, approximately one block from the event.

For questions, contact Parade Chairman Todd Hetrick at 301-616-6344. Participating departments can RSVP using the QR code on the accompanying flyer.

Help us celebrate Oakland Volunteer Fire Department—100% volunteer since 1894!

The Oakland Arts & Entertainment District is proud to present Oakland’s Kick Off to Summer.

Hosted in partnership with the Garrett County Arts Council, the Town of Oakland, and many generous sponsors, this red, white, and blue celebration will bring the community together for a day full of hometown charm and summer fun.

Join us on June 20, 2026, in downtown Oakland for an all-American picnic-style celebration featuring live theatre, poetry, and musical performances that capture the spirit of summer. Stroll through food vendors, local artisans, and craft and retail booths while enjoying classic favorites and festive treats.

Families can gather together and enjoy games, hands-on art activities, and the always-popular dunk tank—plus plenty of kid-friendly fun throughout the day.

Adults can join in the Beer, Hard Seltzer, and Cider Tasting Walk (ticket required). Ticketing details will be announced soon—check back for updates!

Throw on your flip-flops, grab your shades, and soak up the sun—this free, family-friendly celebration is the perfect way to kick off summer in true Americana style!

💗 Downtown Oakland Winter Fest + Wine Walk Returns Feb. 14, 2026

Downtown Oakland is celebrating Winter Fest on Saturday, February 14, 2026, from 10 AM – 4 PM — with a full day of winter fun, family activities, local shopping, and our popular Winter Fest Wine Walk (21+).

Whether you’re coming for ice sculptures, hot cocoa, Valentine photo ops, or wine tastings, Winter Fest is a perfect way to spend the day downtown!

On Saturday, December 13, join us for A Great Small Town Christmas. Enjoy soup served by nonprofit groups at various locations in the Main Street District and take a photo with Santa at the B&O Museum. Gather for a photo at the photo booth after your free sleigh ride. Find discounts and promotions in shops all across town (not just downtown)! Ask about “Elf Cards“ at participating locations where you’ll be entered into a drawing at each shop you spend more than $25 in.

On Saturday, November 29, shop in Oakland for Small Business Saturday. Find discounts and promotions in shops all across town! Ask about “Elf Cards” at participating businesses where you’ll be entered for a unique drawing at each store that you spend more than $25 in!

A Great Small Town Christmas will kick off with a Light Up Night on Friday, November 29th at the Oakland B&O Museum. The event will start with a Walking Holiday Light Parade, led by Santa Claus starting at the Town Parking Lot. All are invited to participate in the walking parade as we make our way to the B&O Museum for the official tree lighting.

American Legion Post 71 will hold a Veterans Day parade in downtown Oakland beginning at 10:30 a.m. Tuesday, Nov. 11. The parade will begin at Liberty Street and travel Second Street to Alder Street and up Third Street to the Oakland Veterans Park at the intersection of Third and Oak Street, where a patriotic ceremony will be held at 11 a.m.

The Town of Oakland and the Greater Oakland Business Association is proud to present the 58th Annual Autumn Glory Grand Feature Parade on Saturday, October 11th at 1pm. ​Be a part of the celebration of the fall foliage season at Garrett County's 58th Annual Autumn Glory Festival Grand Feature Parade, which will be held Saturday, October 11, 2025, in downtown Oakland, Maryland at 1:00 p.m. The title sponsor of the 58th Annual Autumn Glory Festival Grand Feature Parade is First United Bank and Trust

The Maryland State Banjo, Fiddle, & Mandolin Championships have been an Autumn Glory tradition and a great family fun event for many years. We welcome all participants and spectators.

Butterscotch Blonde is a power trio from Cumberland, Maryland, consisting of music veterans Mark Gowans, Brian Plitnik, and Bart Lay.  Formed in 2014, this talented group has been rocking Western Maryland and the tri-state area with a blend of rock, funk, blues, and dance hits. If you love music and you’re ready to let loose and party with the pros, Butterscotch Blonde is your band! Their website is https://www.facebook.com/butterscotchblondeband.

Little Yough Family Flicks - Presents: "Wonka", hosted by Ruth Enlow Library of Garrett County at 7PM on Thursday, August 28th, at Mountain Fresh Farmers Markets, Oakland, Maryland, "Wonka" Is a film about Willy Wonka, a young & poor boy with dreams of opening a shop in a city renowned for its chocolate!n.

The Wild Rumpus is an original string band from West Virginia, specifically calling Fayetteville and Lewisburg home. Led by singer and songwriter Andrew Adkins, their music blends bluegrass, swing, country, and rock & roll, creating a unique sound. Here are some key facts about the band:
- Music Style: Their sound is a fusion of traditional and modern elements, drawing inspiration from artists like Leonard Cohen and Jimmy Martin.
- Discography: They have released three albums on Mudbone Records.
- Live Performances: The Wild Rumpus has performed at notable festivals like Merlefest, Bristol Rhythm and Roots, and the American Music Association.

The West Virginia Brass Quintet, formed in June 2009, is one of the most exciting chamber ensembles in West Virginia.  This versatile group’s repertoire spans five centuries of music, from Renaissance and Baroque to Contemporary to Dixieland Jazz with an emphasis on traditional American music.  With members living more than one hundred and fifty miles apart, the WVBQ goes to great lengths to sustain their passion for music making. From their annual Holiday Residency at the famous Greenbrier Resort to Artist Series Concerts at the Tamarack Center in Beckley and Carnegie Hall in Lewisburg to myriad church services, weddings, and civic functions, the West Virginia Brass Quintet has performed extensively throughout the Mountain State and surrounding areas.Their website is https://wvbrassquintet.com/.

The Wally Gingers Orchestra is Western PA's only remaining original Big Band from the 1940’s, will take the stage. This year, which honors the 35th anniversary of Wally Gingers’ passing and the recent passing of his son, Jim, will feature their favorite arrangement of Wally’s musical gems. These include the timeless Glenn Miller hits of In the Mood, Tuxedo Junction, Pennsylvania 6-500; and other artist such as Benny Goodman’s Jersey Bound; Frank Sinatra’s My Blue Heaven and New York, New York; Bobby Darin’s Mack the Knife; and Woody Herman’s Wood-chopper’s Ball. They’re excited to get this summer season rolling, rolling, rolling!

Megan Jean’s Secret Family is a fresh blend of the 70’s by way of the 90’s rock, soul, country, and jam, emphasizing vocal-driven danceable original songs that bring together generations of sound. In May of 2024, the band made their national radio debut on NPR’s Mountain Stage alongside notable acts like Keller Williams and Bettye Lavette. DC Music Review called them one of their “New favorite acts” following an energitc performance at 2024’s DelFest. The band was awarded a creativity grant from the Maryland State Arts Council to produce their debut full-length album PLOT (Play.Loud.On.Turntable). Their website is www.meganjeanband.com.

Replay is a three-piece band from Western Maryland that focuses on great vintage music from a diverse range of popular musical styles. The local trio started life way back in the early 80’s as the five-piece country/rock group “Luxury Liner” that played frequently throughout Western Maryland, PA and WV. Old timers may remember them from frequent appearances at the Glen Haven Pizza Pub (now Uno’s) on Deep Creek Lake. Having disbanded now over 40 years ago, they reformed in 2022 as the current three-piece group “Replay.” Their meticulous renditions of selections from a wide variety of genres capture the essence of each song performed, allowing the listener to “soak-in” and enjoy the magic of many beloved classics. 

Join us at Broadford Lake Park on July 3 for the annual fireworks show. The Garrett County Community Concert Band will be playing a patriotic set on the new amphitheater before the sun goes down.

The Oakland Arts & Entertainment District is excited to announce Oakland’s Kick Off to Summer event, hosted by the Oakland Arts & Entertainment District in partnership between the Garrett County Arts Council, the Town of Oakland, and many generous sponsors!

This year, on the Summer Solstice of June 21, 2025, expect to see various theatre, circus, magician, poetry, and musical live performances, with more food and craft/retail venders and activities for kids and families, including games, art crafts, the repeated favorite dunk tank, and more! We additionally bring back the popular Beer, Hard Seltzer and Cider Tasting walk (with purchased ticket) and non-profit lemonade stands. 

It’s free fun for all and not to be missed!