10-31-2025 10:00am

DAYTRIPS: Autumn-

10 Autumn-Ready Maryland Towns For A Weekend Retreat

Maryland’s scenic landscapes transform into a breathtaking tapestry of gold, amber, and scarlet as fall settles in, making it the perfect time to explore its charming small towns. From the rolling hills of the Piedmont to the quiet shores of the Chesapeake Bay, the state offers a variety of cozy destinations where crisp air, crunchy leaves, and seasonal flavors set the tone for an unforgettable weekend escape.

Autumn in Maryland means apple picking in historic orchards, sipping spiced cider at local farmers' markets, walking through corn mazes and pumpkin patches, and leaf-peeping vibrant forests ablaze with color. Whether you crave outdoor adventure in Cumberland or peaceful waterfront views in Oakland, these autumn-ready Maryland towns make for a perfect weekend retreat, showcasing the Old Line State's fall magic.

Havre De Grace

Havre de Grace is a beautiful town at the Susquehanna River-Chesapeake Bay confluence, which earns a new lease of life in autumn as the countryside gradually changes color and the community ushers in the season with fun festivals. Dazzling shades of mustard, amber, and crimson blanket Susquehanna State Park, luring leaf-peepers to experience the magical scenery along quiet trails covered in crunchy leaves. Furthermore, you can delight in the crisp air at Millard Tydings Memorial Park, which has peaceful walking paths overlooking the mouth of the Susquehanna River.

The Fall Harvest Festival is one of the best times to visit Havre de Grace. It helps spread the cheer in the community through pumpkin displays, craft exhibitions, food vendors, apple cider tastings, and live music in downtown. Lastly, you can spend the night at Vandiver Inn, a short walk from the Chesapeake Bay.