Here is a fun one to spring on the kids in the car: you can take a day trip to Florida without leaving New England. Florida, Massachusetts sits about 55 minutes and 31 miles south of Valley View Villa via VT Route 100 S, high in the Hoosac Range along the Mohawk Trail — and it is one of the coldest, snowiest, most mountainous towns in the whole state. No palm trees, no pelicans, no Miami Beach valet line. Just a wall of Green Mountain views, a haunted railroad tunnel, and a bronze elk keeping watch over the Deerfield Valley.
Wait, There Is a Florida in Massachusetts?
There is, and the name is the best kind of geographic joke. When the town was incorporated in 1805, the United States was negotiating to buy the territory of Florida from Spain, and the news was full of that flat, tropical land of palms and pelicans. So the mountain village borrowed the name — then grew into a place where the town center sits nearly 1,900 feet up and the snow piles deep. Pack a fleece, not a swimsuit.
Whitcomb Summit and the Elk on the Trail
The centerpiece of a Florida, Massachusetts visit is Whitcomb Summit, the highest point on the Mohawk Trail at 2,240 feet. There is a paved pull-off right along Route 2 where you can stop, stretch, and take in long views of the Green Mountains to the northeast and the Hoosac Range rolling away to the southwest. Standing guard over the overlook is the Elk on the Trail, an eight-foot bronze elk on a rough granite base, dedicated in 1923 to honor members of the Massachusetts Elks who died in World War I. It is free, easy to reach, and a striking spot to watch the light cross the valley.
The Hoosac Tunnel — the “Bloody Pit”
A few minutes downhill lies one of the most fascinating and sobering pieces of engineering history in New England. The Hoosac Tunnel runs almost five miles straight through Hoosac Mountain, and when crews finished it in 1875 after 24 years of digging, it had earned the grim nickname the “Bloody Pit” — nearly 200 workers died during construction, including 13 lost in a single 1867 explosion in the central ventilation shaft. It remains the longest active transportation tunnel east of the Rocky Mountains, and freight trains still rumble through it today.
You can glimpse the east portal from the River Road area near Whitcomb Hill Road, and the dark stone archway with its 1877 keystone is a striking sight. One firm word of caution though: this is a live rail line, and trains round the curves quietly. Admire it from a distance, keep the kids close, and never step onto the tracks or into the tunnel itself. The lore and the history are the draw here, not the tunnel interior.
Driving the Mohawk Trail
Half the fun is the road itself. The Mohawk Trail — Route 2 — was dedicated in 1914 as one of the country’s first scenic auto roads, and the stretch over Whitcomb Summit is the high point in every sense. To make a bigger loop, keep heading west down the mountain into North Adams, home to MASS MoCA, one of the largest contemporary art museums in the country.
Planning Your Florida, Massachusetts Day Trip
This one pairs beautifully with an active morning. The Deerfield River rafting sections run through this same corner of the map — rafters even nicknamed a sandy beach on the run “Miami Beach” after this decidedly un-tropical town — so a group can raft in the morning and cruise the summit after. Pack a picnic for the Whitcomb pull-off, bring layers even in summer, and time it for late September or October if you can — the foliage along this ridge is some of the best in New England. Then it is an easy hour back to the hot tub and pond at the villa.
🗺️ More to Explore Near Mount Snow
- Whitewater Rafting Near Mount Snow — pair the summit with a morning on the Deerfield
- Day Trip to Brattleboro, VT — another easy day out from West Dover
- Day Trip to Bennington, VT — history, art, and mountain views
- Covered Bridges of Southern Vermont — a scenic driving tour closer to home
Frequently Asked Questions
Why is there a town called Florida in Massachusetts?
The town was incorporated in 1805, right when the United States was negotiating to purchase Florida from Spain and the name was in the news. The mountain village adopted it — an irony that has only grown, since it is now one of the highest and snowiest towns in the state rather than a tropical one.
How far is Florida, Massachusetts from Mount Snow?
It is roughly 55 minutes and 31 miles from the West Dover area, mostly a straight shot south on VT Route 100 before you climb up onto the Mohawk Trail. It makes an easy half-day or full-day outing from a stay at Valley View Villa.
Can you go inside the Hoosac Tunnel?
No. The Hoosac Tunnel is an active freight rail line, and walking onto the tracks or into the tunnel is both dangerous and illegal. You can view the east portal from a safe distance near River Road, but keep well clear of the rails.
Is Whitcomb Summit free to visit?
Yes. There is a free paved pull-off along Route 2 at the summit, and the Elk on the Trail monument and overlook are open to the public at no charge. It is a quick, rewarding stop for anyone driving the Mohawk Trail.
When is the best time to drive the Mohawk Trail?
Fall foliage season, roughly late September through mid-October, is spectacular along this high ridge. Summer is a close second, with clear, long-range valley views and comfortable temperatures at elevation.
