Middlebury, Connecticut: Quassy, the Greenway, and the Quiet Side of the Valley
Middlebury, Connecticut
Pictures from Middlebury
See all 4 photos →
Middlebury was incorporated in 1807 from pieces of Southbury, Waterbury, and Woodbury — named simply for sitting "in the midst" of them — and it has stayed the quiet neighbor ever since: farms, a green, a boarding school designed by pioneering architect Theodate Pope Riddle, and one glorious exception to the calm. That exception is Quassy, the 1908 lakeside amusement park on Lake Quassapaug that began as a trolley-line resort and never stopped running. Come for a family day at the park, bike the old trolley route, and eat far better than a town of this size has any right to feed you.
-
sight
On Lake Quassapaug since 1908 and still family-owned — 20-plus rides including the Wooden Warrior coaster, plus the Splash Away Bay waterpark. Seasonal, roughly April through October.
-
walk
4.5 paved miles along the old trolley roadbed that once carried summer crowds to the lake — hilly, bench-lined, and it ends near Quassy's gates.
-
Local history in an 1897 two-room schoolhouse near the Green, a National Register building that spent decades as the town library.
-
The fine-dining pick: contemporary American on a site with a family restaurant legacy back to the 1940s.
-
House-brewed beers, a full kitchen, and a patio — the easy crowd-pleaser.
-
food
Hand-tossed pizza and 26 rotating drafts.
-
food
Breakfast from 6:30 AM daily — eggs Benedict and French toast are the moves.
-
food
The famously enormous menu; there is something for every person in the car.
-
food
Family-run Mexican from one of Connecticut's oldest family Mexican restaurant groups.
From trolley resort to family park
A trolley line reached Middlebury by 1908 and turned Lake Quassapaug into a summer resort — swimming, picnicking, dancing, and a carousel. That resort became Lake Quassapaug Amusement Park, today's Quassy, purchased in 1937 by three Waterbury businessmen. The trolley itself shut down in 1930 after Route 64 was improved; its roadbed is now the Middlebury Greenway, so you can ride the route the summer crowds once did — on two wheels. In 2026 an industry index named Quassy the most affordable theme park in America.
Where to stay
Middlebury itself has no verified operating hotel or B&B as of 2026 (the longtime Tucker Hill Inn appears to have closed). The closest verified bases are the Courtyard by Marriott in downtown Waterbury, ten minutes east, or the resort-style Heritage Hotel in Southbury, ten minutes southwest — both covered in their towns' Ethos guides.
Frequently asked questions
- Is Quassy open all year?
- No — Quassy is seasonal, operating roughly April through October, with the Splash Away Bay waterpark in summer.
- Is the Middlebury Greenway good for kids?
- It's paved and car-free for 4.5 miles along Route 64, though notably hilly in stretches — fine for confident young riders, with benches along the way.
- Where do I stay for a Quassy trip?
- In neighboring towns: downtown Waterbury's Courtyard by Marriott or Southbury's Heritage Hotel are the closest verified options, each about ten minutes away.
- What's Middlebury's history in one line?
- Incorporated in 1807 from parts of Southbury, Waterbury, and Woodbury, it stayed agricultural — dairy and saddle horses — while its neighbors industrialized.
- What is Westover School?
- A girls' boarding school established in 1909, designed by Theodate Pope Riddle, one of America's first licensed female architects.
Some booking links on this page earn Ethos a commission at no extra cost to you.