Every Fall, This Tiny Town in Maryland Holds One of the Best Autumn Festivals in America

For a smaller town, the following area in Maryland goes big when it comes to its annual autumn festival. This large event may be one of, if not THE best, autumn festivals in America. It's undoubtedly one of the very best fall festivals in Maryland—really! Read on to learn more about this multi-day event and consider joining in on the fun festivities. If you've been looking for things to do in Maryland in the fall, this one is a fantastic choice. Read on to learn about all the fall fun!

Ready for all things autumn? Then head west to the historic mountain town of Oakland, Maryland, which hosts the annual Autumn Glory Festival in October. This little mountain town, with a population of under 2,000, is always charming, and it's especially sweet as the leaves begin to change.

And things become very festive when the town's annual autumn event rolls around. How could they not in such a classic autumn atmosphere? This multi-day event will feature plenty of things to see and do. Don't miss out on the parade, with all sorts of handmade autumn floats and other local businesses, schools, and silly scenes that all ages will surely enjoy. This year's Autumn Glory Festival will be held October 8-12, and 2025 marks the event's 58th year, so mark your calendars and make plans to attend!

Other Autumn Glory Festival events include a craft show, car show, horseback trail rides, live music, a farmers market, and even a carnival! While in the area, you can also go on a fall foliage driving tour to really appreciate just how gorgeous this town is during the month of October. You'll love it! Just remember to bring your camera!

Learn more about this amazing fall festival in America by visiting the website below. Enjoy! It's bound to become one of your favorite Maryland festivals.

Visit the Maryland's Autumn Glory Festival website for dates and a schedule of events throughout the festival, including the annual Turkey Dinner, the parade, farmers' market, corn maze, car show, the can't-miss parade, and more! This will help you plan to partake in as many events as you can.

If you are looking to stay a while, take a look at all the fun activity options and attractions on the TripAdvisor Booking/Experiences website. For accommodations in Oakland, book a stay at this cheerful stone cottage, which is located just two minutes from Deep Creek Lake. Another option is an incredibly cozy woodland cabin by Yough River Resort. Just imagine the fall foliage you'll see here this October!

Along with having the best autumn festival in America, the small historic town of Oakland is also a wonderful place for a weekend winter getaway in Maryland. So, if you miss taking a trip to Oakland this fall, there's always next season!

Plan your own trip to Maryland this fall with Only In Your State’s AI-powered itinerary planner.