Middletown Heritage Festival
Celebrate the history, traditions and community spirit of Middletown with a full day on Main Street featuring the Heritage Parade, live music, activities, local organizations and more.
Honoring the history of Middletown while celebrating the community that continues to shape its story today.
Celebrate community spirit on Main Street.
The 2026 Middletown Heritage Festival returns Saturday, September 26, bringing neighbors, organizations, businesses and visitors together for one of Middletown’s most cherished traditions.
From the Heritage Parade and live entertainment to local exhibits, family activities and community organizations, the festival offers plenty to discover throughout the day.
Main Stage Schedule
Enjoy an afternoon of live music in the heart of the festival.
The Martin Brothers
The Martin Brothers, often performing alongside Aspen Run, are a family-centered traditional bluegrass band based in Maryland. Known across the Mid-Atlantic region for high-energy, straight-ahead acoustic picking and tight brother harmonies, their sound is heavily influenced by bluegrass legends including Jimmy Martin, The Stanley Brothers and Bill Monroe.
Milk Mountain
Milk Mountain is a ’70s-through-2000s rock and pop cover band with an extensive catalog spanning a wide range of genres and artists. Their repertoire includes music from David Bowie, Elton John, The Police, No Doubt, Soundgarden, Bruno Mars, Smashing Pumpkins and more.
Special Delivery
The Special Delivery Band is a classic rock and dance cover band performing throughout the Frederick, Maryland area.
Festival Activities
Explore the parade, community exhibits, festival traditions and special activities happening throughout Middletown.
The Middletown Heritage Parade
The Heritage Parade kicks off the festival with the Frederick County Honor Guard leading the procession down Main Street from Prospect to Willow. Dance groups, floats, marching bands and community organizations make the parade a highlight of the day. Parade participants will stage along Main Street from Cone Branch to Prospect.
2026 Parade Grand Marshal
The 2026 Heritage Parade Grand Marshal is TBA. Watch the official Middletown Heritage Festival website for updates as the festival approaches.
Heritage Festival Booth
Location: Main Street in front of Town Hall
Stop by the Middletown Heritage Festival booth for festival merchandise and keepsakes including mugs, T-shirts and more.
Festival merchandise is also available year-round through the festival’s online store.
Middletown Volunteer Fire Department
First Aid Station & Safety Information
Corner of Main & S. Jefferson Street
The Middletown Volunteer Fire Department will share important fire and personal safety information for both children and adults, including home safety, bicycle safety and the “Close Before You Doze” program.
Visitors can also check out apparatus on display and speak with local firefighters and EMTs.
Christ Reformed UCC
Christ Reformed UCC will host activities at the church, including a bounce house and bake/craft table.
Welcome Center Heritage Exhibit
19–21 West Main Street, Middletown
Main Street Middletown has worked with Commissioner Larry Bussard to select objects and photographs from his collection for a special commemorative exhibit.
This special exhibit will be available only during the Heritage Festival.
The 2026 Collectible Ornament
The 20th ornament in the Christmas in the Valley series commemorates America’s 250th anniversary and imagines Middletown as it may have appeared in 1776 — just nine years after German settlers first laid out the town in 1767 at the base of South Mountain.
Log cabins line a snow-covered street beneath the mountain’s familiar silhouette. A flag marks the birth of the nation, while Santa appears in a deep green robe inspired by old-world traditions.
Parking, Shuttle & Road Information
A little planning will make your festival day even easier.
Festival Parking
Parking is available off School House Drive on the school campuses.
Prior to the parade, visitors will need to walk down Main Street from the parking area to the festival.
Jumbo’s Shuttle
The festival has teamed up with Jumbo’s Pumpkin Patch to provide a convenient hay wagon shuttle.
Shuttle service begins after the parade and runs throughout the day. Stops are marked and are also noted on the festival map and brochure.
Road Closures
Main Street: Closed approximately 6:00 AM–8:30 PM on festival day.
For the parade, approximately 6:00 AM–12:00 PM: Main Street will be closed from Coblentz to North Point Terrace.
The festival area includes Main Street from Schoolhouse Drive to Willow Street. Side streets within the festival area will also be closed.
Visitors should review the official festival map and website before traveling for the latest parking, shuttle and closure information.
Get Involved
Businesses, community organizations, parade groups, vendors and volunteers all help bring the Heritage Festival to life.
Volunteer at the Festival
The Heritage Festival is possible only with the help of volunteers. If you can give a few hours to help bring this community tradition to life, festival organizers would love to hear from you.
General volunteering:
rjjkna@aol.com
Volunteers are especially needed to assist with merchandise sales at the Heritage Festival booth.
Heritage Festival booth:
mtownheritagefestival@gmail.com
Food vendors interested in participating may also contact Jennifer Ross at rjjkna@aol.com .
There’s a place for everyone in the parade.
Showcase your business, ride on a float, march with a band, walk alongside your team, organization or community group — or simply join the crowd along Main Street and cheer them on.
Help Bring Main Street to Life
Bring your creativity, energy and pride in the community. Participating in the Heritage Parade is an opportunity to celebrate what makes Middletown special while sharing your business, organization, team or group with the community.
And don’t forget — there will be prizes!
Celebrate Middletown.
Celebrate its heritage.
Make plans to join the community on Saturday, September 26, 2026 for the Middletown Heritage Festival. For festival updates, maps, participating vendors, applications and additional information, visit the official Heritage Festival website.
More Festival Information
