In many ways, Oakland is the heart of our county. It is not only the county seat; it is also home to a variety of vibrant businesses and unique events that offer something for everyone to enjoy.

Essential to the work and mission of the town is the Greater Oakland Business Association (GOBA), which works in conjunction with the Mayor and Town Council to help small businesses in the area.

In addition to providing assistance to both potential and current business owners with economic incentives and other resources, GOBA also coordinates a number of events held in Oakland celebrating all the seasons of the year.

In February, GOBA will hold its annual Winterfest Celebration, held each year on President’s Day weekend with fun for the entire family. Guests can enjoy a leisurely stroll downtown while listening to live music. There will be indoor and outdoor activities for kids, including a “Story Walk” where participants can read a deconstructed version of “The Snowy Day”, while strolling from shop to shop.

One of the most popular features of the event is the Wine Walk, where participants can visit six different businesses throughout downtown Oakland and enjoy delicious wine tastings.
Guests can enjoy two pours at each stop and will also have the opportunity to buy more by the glass or bottle. Merchants will choose their own wines but will include both local and national varietals. Tickets are $15 and will sell out, so make sure to buy yours ahead of time.

Be sure to stop at the historic B&O Train Station (a wine tasting stop) to learn more information about the upcoming Sesquicentennial celebration, a year-long homage to the 150th Birthday of Garrett County. Visit to view a complete schedule and map of the wine stops.

As fun as winter can be in Garrett County, summer is truly when things kick into high gear. GOBA and the town of Oakland feature several different festivals to highlight our area’s cultural and artistic talent. On Saturday, June 18, GOBA will host the third annual Kickoff To Summer, a fun downtown event featuring live music, sidewalk sales, artists exhibits, kids activities and a Beer Walk (set up similarly to the Wine Walk at Winterfest). The popular Farmers Market will be held that morning in the Mountain Fresh Pavilion with plenty of fresh produce and crafts on hand for sale. Coinciding with Father’s Day weekend, bring your favorite dad to town to participate in the CornHole Tournament, enjoy some live music and enjoy the vintage automobiles in the Car Show.

Beginning on Thursday, June 9th, the Little Yough Family Flicks (formerly Pocket Park movies) will begin. Each Thursday from mid-June through mid-August, families can enjoy a fun movie under the Pavilion. Movies begin at dusk and are free of charge. Bring your own blankets, lawn chairs and snacks. Sponsored by local businesses, this year organizers plan to have some fun treats for children in attendance.

One of the most popular summer events in the area is the Little Yough Summer Music Festival held every Friday evening through Labor Day weekend beginning on July 9th. According to GOBA Coordinator Nicole McCullough, bands have already been booked for summer of 2022, including a mix of new bands and some local favorites. Organizers work hard to present a variety of musical styles. The slate for 2022 will cover all genres of music including reggae, big band, blue grass & country. “We try to bring in a wide variety of music, including some you may have never heard before,” explains Nicole.

The concerts are held rain or shine under the Mountain Fresh Pavilion. Bring a lawn chair, blanket and cooler with your favorite drinks. The concerts begin at 7 PM, but local food vendors will be on hand starting at 6 PM. Concerts are free, however donations are appreciated.

This year marks the 25th anniversary of the Festival, and coordinators are planning some extra special events to commemorate this milestone. Nicole is also looking at local musicians and school groups to perform on concert night as opening acts.

Of course, autumn is the most spectacular season in the area, and Garrett Countians make the most of it with our annual Autumn Glory Festival. Although events are held throughout the county, Oakland is the center of the fun with GOBA hosting some of the most popular aspects of the festival including the 100 unit parade. Scheduled for Saturday, October 15th this year, the parade features clowns, floats and marching bands from around the region.

GOBA will also host the Maryland State Banjo, Fiddle & Mandolin Championships on Friday & Saturday, October 14 & 15 at Southern High School in Oakland. On Friday, enjoy banjo and mandolin players from all over the state and beyond. Saturday night is the fiddle contest with both money and bragging rights up for grabs. Anyone who loves Appalachian music will not want to miss this event.

As the holiday season approaches, the town of Oakland gears up for Christmas with Black Friday and Small Business Saturday sales. The official kickoff to the season is held the first weekend of December with events for the entire family.

Friday, December 2nd is Light Up Night. Santa will lead the way beginning at Oakland town parking lot where local children and their parents can join him as he parades through the town to the B&O Train Museum. There, he will light the town Christmas tree. Participants can enjoy hot chocolate and cookies to end the evening while mom and dad snag some great deals from local merchants.

On Saturday, December 3rd, visit downtown Oakland for Soup and Santa. Local non-profit organizations will set up outside area businesses and serve samples of delicious hot soup to enjoy while you’re shopping. Carriage rides are provided by Pleasant Valley Dream Rides and Santa will be available for visits from local children. Saturday’s event is held in conjunction with the annual House of Hope food drive, and downtown Oakland will be bustling with Christmas spirit (and great specials).

Of course, these events need lots of help to be successful, and GOBA members are always looking for volunteers. Volunteers are needed to join one of their five committees which include: the Clean & Green Committee, which focuses on the beautification and preservation of the town; Promotion & Marketing; the Events Team; CityScapes which works on landscaping and physical appearance; and the Economic Vitality Committee which works to expand the economic base of the town and brind in new businesses to Oakland.

GOBA also need help staffing its various events. “We are always looking for volunteers, and any townspeople are welcome to join us. We also offer service learning hours for local students who want to get involved,” says NIcole.

Of course, the main mission of GOBA is to promote and help local businesses, and to that end, they have several programs that can be tailored to the needs of individual merchants. “Because of these programs, very few businesses had to close their doors during the pandemic, and each season sees new businesses opening,” says Nicole. “We will work closely with our business owners to help them in any way we can,” she adds.

Some current incentives include reduced taxes and collection fees, help with advertising costs (including signage), reduced utility connection fees, and a 50% match for money spent on facade and outside improvements.

If you’ve ever dreamt of opening your own business, the town’s website has a host of resources to help get your started. Some of the topics included offer assistance on applying for correct licensing for your business, links to other county agencies including Garrett County Business Development and the Small Business Development Center as well as information on funding opportunities.

The GOBA Board of Directors meets each month, and while membership meetings have been paused because of COVID, officials are hoping they will resume in 2022.

For more information, including a complete calendar of town events, visit the Oakland website at See you in Oakland…a great small town!

Written by Linda Carr