Just 20 miles west of Boston, Ashland Massachusetts blends small-town charm with a refreshingly modern vibe. Surrounded by forests, lakes, and trails, yet home to innovation, arts, and adventure, it’s the kind of place where you’ll come for the scenery—and stay for the surprises.
Start your visit with a walk through Warren Woods or along the shores of Ashland State Park, where you’ll find 470 acres of swimming, boating, biking, and peaceful woodland trails. The town’s deep connection to nature is hard to miss—whether you’re birdwatching or simply catching your breath.
History buffs will love Marathon Park, a tribute to Ashland’s role as the original starting line of the Boston Marathon. Today, the site draws runners from across the region for races and photos at the commemorative granite monument, honoring a legacy of endurance and pride.
Ashland’s roots stretch back even further—long before it became a residential suburb with a modern twist, it was a stop along the ancient Bay Path and home to the 17th-century Native community of Magunkaquog. The town later made its mark on the modern world thanks to Henry Warren’s invention of the electric clock, earning the local high school teams the nickname “Clockers.”
Photography by Paul Beaudoin
But Ashland doesn’t rest on its history. It’s a community that creates. One of the best examples? The Corner Spot, a cheerful public space where new businesses debut as pop-ups, neighbors gather for live music or local festivals, and kids swing while their parents sip coffee. If you’re in town this May, don’t miss Earth Day Fest (May 10) or Culture Fest (May 31)—two lively events celebrating sustainability, food, music, and community.
When you’re ready to refuel, options abound. Ashland Ale House serves up reliable comfort food with a strong beer list, while Stone’s Public House pairs Irish-American fare with a storied (and possibly haunted) history dating back to 1832. For a sweet twist, visit Sub Zero Nitrogen Ice Cream, where your custom creation is flash-frozen with a puff of liquid nitrogen—fun for all ages and surprisingly delicious.
And there’s more for those who crave action: try slot car racing at Modelville Hobby, a hands-on blast from the past that kids and adults will both love. Or embrace the latest craze at Clocktower Pickleball, a four-court indoor facility with hourly play and a bar to keep the good times rolling. Still have energy? Gear up for a high-stakes round of paintball at Boston Paintball, home to the newest, most versatile movie set style playing facility on the East Coast. Apocalypse City has 23 buildings of varying sizes and levels complete with an airplane, a tank, a police car, an ambulance and an Army Deuce. Or head to Dr. Greens Golf & Entertainment, where the indoor golf simulators bring the green to you.
Prefer a slower pace? Schedule a meditation or reiki session at Ashland Reiki & Wellness, a calming spot for those seeking connection, clarity, or a simple deep breath. Nearby, the Ashland Farmers Market (Saturdays, June through October) offers fresh local produce, baked goods, live music, and themed events like “Dog Day”—all nestled in the park at 125 Front Street.
Shopping in Ashland is all about supporting small businesses. Find thoughtful gifts and beautiful florals at Blush Bouquets, or explore unique home goods and cozy finds at Good to Be Home. Visit Dulce D Leche for stellar handmade chocolates as well as other sweet treats.
Book a room for the weekend at the Warren Conference Center & Inn, a hidden gem. Surrounded by woods and perched on a private lake, it’s a peaceful place to unwind—complete with fire pits, lawn games, and warm hospitality that makes it feel like a retreat.
With its creative energy, rich history, and love of community, Ashland is the kind of place that feels like home—even if you’re just passing through for the weekend.
