Route 5 — The Connecticut River Byway

A River’s Journey

The Connecticut River Byway spans 500 miles across Vermont and New Hampshire, with Route 5 tracing the Vermont side of this magnificent waterway. As you travel north from Brattleboro, you’ll be treated to breathtaking river vistas, rolling farmlands, and charming historic towns that tell the story of the region’s development.

The landscape showcases nature’s artistry through terraced hillsides, fertile floodplains, and the dramatic slopes of the surrounding mountains. Each season brings its own splendor—spring’s vibrant greenery, summer’s lush abundance, autumn’s legendary foliage, and winter’s serene snowscapes.

Living History

The Connecticut River has shaped life in this valley for centuries. Historic buildings, covered bridges, and working farms tell the story of how this waterway has sustained communities through changing times. The agricultural heritage remains vibrant today, with farms offering seasonal produce, maple products, artisanal cheeses, and other Vermont specialties.

Many historic sites along the byway are open to visitors, providing insights into the area’s fascinating past. From colonial settlements to industrial developments, the river’s influence on regional history is evident at every turn.

Four-Season Recreation

Whether you’re seeking adventure or relaxation, the Connecticut River Byway offers recreational opportunities year-round. In warmer months, enjoy fishing, kayaking, and canoeing on the river, or explore the numerous hiking trails that offer spectacular views. When snow blankets the landscape, nearby ski areas and winter trails become the focus for outdoor enthusiasts.

Your Journey Awaits

As you travel Route 5, take time to slow down and savor the experience. Pull over at scenic overlooks, visit local farm stands, explore the walkable downtowns, and connect with the people who make this region special.

The Connecticut River Byway isn’t just a route from one destination to another—it’s a journey through the heart of what makes southern Vermont unique. Every mile offers new discoveries and the opportunity to create lasting memories of Vermont’s natural splendor and warm hospitality.