Woodbury

Country Riverfront

Population: 10k

Cost of Living: Moderate

Near Train: No

Near Bus: Yes (CTtransit local bus service in the region; limited regional bus connections Line)

Woodbury sits in western Connecticut as a town that still feels organized around its center rather than around a highway exit. A newcomer notices the steady rhythm of old houses, church steeples, and local businesses along Main Street, with the town green giving the place a clear focal point. It has the look of a community that grew up around roads, farms, and small civic institutions, and it still carries that scale: walkable in the center, quieter and more spread out at the edges. The surrounding landscape is part of the appeal, with wooded hills, stone walls, and stretches of countryside that make the town feel removed from the rush of larger places nearby. Woodbury is also known for its antiques scene, which gives the downtown a browsing, weekend-visitor energy without turning it into a resort town. Daily life here tends to be practical and local, with residents relying on nearby services in town and in neighboring communities. The pace is measured, and the setting rewards people who like a place where the landscape is visible and the center of town still matters. In autumn, the roads and back lanes can feel especially scenic, while winter brings the more familiar New England mix of cold mornings, gray skies, and the occasional heavy snowfall. It is the kind of town where errands can turn into a slow loop past historic buildings, small shops, and quiet residential streets, and where the sense of place comes less from spectacle than from continuity.

CitizenM
Learn More

It's impossible to confuse citizenM with any other hotel. We don't look or sound like anyone else. Bold, vibrant, and artistic - that's us. Our rooms cater to modern travelers - enormous ultra-comfortable beds, unlimited free Wi-Fi and 24/7 food and drinks always waiting at canteenM. And best of all, our ambassadors are every guest's best friend.

CitizenM

Keep reading. It is free.