Fall in Massachusetts has a magic all its own. The air turns crisp, the trees blaze with color, and the smallest towns come alive with seasonal charm. In Littleton, that means everything from apple picking to festive Halloween fun for the whole family.
Whether you’re after outdoor adventures, cozy afternoons, or classic autumn activities, Littleton offers plenty to enjoy as the days grow cooler. Here are some of our favorite fall experiences in this special corner of Massachusetts.
Apple Picking Near Littleton
New England has some of the country’s most beautiful apple orchards, and Littleton is surrounded by some of the best spots to pick your own.
- Doe Orchards is a local gem—quiet, peaceful, and beautifully maintained. Pick your own Honeycrisp, Gingergold, and Gala apples. You can also buy peaches at the orchard’s foodstand.
- Nashoba Valley Winery offers a unique combination of apple picking and wine tasting. The attached brewery and distillery offer something for every taste.
- Shelburne Farm in Stow has pick-your-own apples, peaches, and Asian pears, warm cider donuts, hayrides, playgrounds, and plenty of family-friendly charm. Don’t leave without trying their signature cider donuts.
From fun outings with friends to sweet family adventures, apple picking is the kind of Littleton tradition that makes fall memorable. Bring a tote bag and be sure to dress in layers for the crisp New England weather.
Witches Woods: A Seasonal Favorite
Witches Woods celebrates the spooky spirit of New England during the Halloween season. Located in nearby Westford at Nashoba Valley Ski Area, this seasonal event turns the ski slopes into an eerie backdrop for thrills and chills.
The signature attraction is a haunted hayride that pulls guests through woods filled with live actors and special effects. Meanwhile, themed haunted houses and mazes are enough to make even the bravest souls shiver. But there’s also plenty to do for the faint of heart, thanks to carnival games and live entertainment.
Tickets are sold in advance and sell out quickly. Book early for Friday, Saturday, and Sunday openings, which draw both locals and visitors from across New England.
Hiking Trails With Fall Foliage Views
The fall foliage is one of Massachusetts’ greatest natural treasures, and around Littleton, you’ll find hiking trails that showcase it at its best.
- Oak Hill is a moderately challenging hike with lookout points like Lookout Rock, dramatic features like Tophet Chasm, and historic old roads to stroll along.
- Nagog Hill Orchard offers gentler terrain among maple and oak trees, including a small working orchard and views across the surrounding hills.
- Great Brook Farm State Park in Carlisle has over 20 miles of trails through fields and woods, a working dairy farm (weekend tours available), and an ice cream stand, perfect for after a hike.
Be sure to dress for the conditions, as cloudy days can bring a brisk chill. Put on your hiking shoes, bring a camera, and get ready to capture some of New England’s most stunning foliage.
Local Fun Runs and Outdoor Events
Why wait for the new year to get in shape? Littleton is full of fitness activities and outdoor events right in town, and fall is no exception.
The Littleton Road Race is a September staple, combining competitive running with community spirit for a good cause.
Throughout the fall, schools and community groups host even more charity walks and outdoor gatherings. Bookmark the Littleton town calendar to find activities that fit both your lifestyle and the fall spirit, from bluegrass concerts to mindfulness and meditation classes.
Stop by Collective Cannabis in Littleton
After a full day of apple picking in Littleton, hiking, or braving the haunted hayride at Witches Woods, relax, unwind, and enjoy the season closer to home. For a dispensary near Littleton, look no further than Collective Cannabis, located at 537 Great Road, just minutes away from the area’s best fall activities.
A carefully curated selection will help you keep the good vibes of fall going. Our menu ranges from flower to concentrates to edibles. We’ll help you find the right strains to complement your fall calendar, whether you need to keep calm at a haunted house or recover like a pro from a charity run.
Collective Cannabis is committed to making your store visit as pleasant as a day in the apple orchard. That makes us the perfect stop for a fall visit to the area, whether you’re new to cannabis or already know what you’re looking for. Make Collective Cannabis your stop in Littleton this fall season.
