Part road trip, part treasure hunt, part excuse to spend an October day wandering Hampshire County.
You might find pumpkins at one stop, something delicious at the next, a local maker around another bend, and a place you never knew existed before the day is over.
There’s no starting line. No required route. No wrong way to crawl.
Choose the stops that tempt you and build your own fall adventure.
Some of Hampshire County’s best discoveries are hiding beyond the main road.
Wear real shoes.
October and rural terrain occasionally conspire against cute footwear.
Download what you need.
Cell service can get sketchy once the mountains start doing mountain things.
Bring a little cash.
Not every stop operates like a suburban shopping center.
Give yourself time.
Hampshire County miles are prettier when you don’t rush them.
🐾 Leave your pets at home.
For the safety and comfort of visitors, animals, and participating properties, pets are not permitted at Fall Crawl stops.
Remember where you are.
Many stops are working farms, businesses and private properties. Follow posted directions and respect boundaries.
Hampshire County deserves more than a drive-through.
Stay the night, wake up somewhere beautiful and give yourself another day for mountain roads, local food, history, trails and whatever you didn’t manage to squeeze into Saturday.
