Massachusetts' Under-The-Radar Town Has Scenic Highways, Trails, And Berkshire Mountains Views

With its picturesque towns and wooded mountain scenery, the Berkshires region in Massachusetts is one of New England's most iconic fall destinations. But the region is a pleasure to visit in all four seasons, offering skiing and snowboarding in winter, quiet hikes in spring, and cultural events in summer, when the Boston Symphony Orchestra temporarily relocates to Tanglewood, a live music venue just outside of Lenox. 

One lesser-known spot to seek out is Florida, a perhaps counterintuitively named, under-the-radar Massachusetts town offering easy access to scenic drives and hikes with mountain views. Overlooking the Berkshire Hills at an elevation of 2,180 feet, Florida is located in Northern Berkshire County, not far from the border of Vermont. The small town of 774 residents, according to Census Reporter, is positioned on the Mohawk Trail Scenic Byway, one of Massachusetts' most beautiful drives. Formerly a footpath used by the region's Native American tribes, the byway (also known as Route 2) runs about 63 miles from North Adams to Millers Falls. 

Visitors can start enjoying it on the short but picturesque drive along mountain roads to North Adams, about 15 minutes northwest of Florida. North Adams, an artsy New England gem with cozy cafés (like the stylish Steeple City Social and the popular Eagle Street Cafe), is also home to the wonderful Massachusetts Museum of Contemporary Art (Mass MoCA, admission $25 for adults and $10 for kids). Together, Florida and North Adams have everything you need for an idyllic weekend away from the city without the downsides that come with being isolated far out in nature. 

While heading out of North Adams on the Mohawk Trail Scenic Byway, don't miss the famous Hairpin Turn, offering panoramic views over the Hoosac Valley and Mount Greylock, Massachusetts' highest point. Continuing on Route 2 past Florida, continue the scenic drive for about 30 minutes to Shelburne Falls, a historic village known for its fairytale-like Bridge of Flowers. The repurposed trolley bridge, draped with lush greenery, spans the pretty Deerfield River. Just steps away on the riverbank, Juicebox Wine Bar is a lovely spot to enjoy a glass of wine with views of the town's landmark bridge.

Back in Florida, park the car and explore the Berkshires on foot. From the South County Road Trailhead, hike a 4.5-mile trail through Savoy Mountain State Forest. Framed by beech-maple forests, the trail crosses brooks and passes peaceful ponds, the mountains looming in the distance. 

Or start at the Dunbar Brook Trailhead for a hike or cross-country skiing adventure through Monroe State Forest, which is a great place to catch views of local songbirds. The trail is 7 miles out-and-back, and it connects to the Raycroft Overlook, a perfect place to take in panoramic views of the surrounding mountains. 

During a stay in Florida, base yourself at the Blue Vista Motor Lodge (rooms from around $175 per night), a mountaintop hotel right on the Mohawk Trail Scenic Byway. With Adirondack chairs set around outdoor fire pits, and a pair of open-air hot tubs with mountain views, it's a great place to get away from it all. Another option is to rent a cabin or chalet in the area through Airbnb.

Since Florida doesn't have much in the way of dining options, you're better off driving along Route 2 to North Adams. Near the Hairpin Turn lookout, you'll find the historic Golden Eagle Restaurant, a family-run establishment that serves steaks and seafood in a two-story space with striking mountain views. It's open from 4 to 9 p.m. on Friday and Saturday, and to 8 p.m. on Sunday. A few minutes away in North Adams, you'll find many more restaurants, bars, and shops. 

Getting to this green oasis is easy. Florida is a 2.5-hour drive from Boston. Albany and its international airport are closer, about a 1.5-hour drive away, and you'll need a car to navigate the relatively remote region. While exploring the area around Florida, don't miss the chance to head to a hidden waterfall trail to the idyllic Tannery Falls — the trailhead is just a short half-an-hour drive south.