Snake Alley

Snake Alley was laid out in 1894 by a group of Burlington's German immigrants, including a stonemason and others familiar with the switchbacked roads that climbed the steep vineyard hills of the old country. Burlington's bluffs posed a real problem for wagon traffic, and the alley was conceived as a clever way to connect the business district below with the neighborhoods above without a punishing straight climb.

The design packs several sharp switchbacks and half-curves into a very short, very steep block, paved in tilted brick set to give horses' hooves a grip. It was ambitious and picturesque, but the tight turns proved hard on horses and wagons, and the idea was never widely copied. Instead the street became a landmark in its own right, long advertised as the crookedest in the world, a claim it shares in friendly rivalry with a famous street in San Francisco.

Burlington grew up as a busy river port and rail town on the Mississippi, and its steep bluffs shaped how the city was built, with streets climbing and switching back to reach the heights above the water. The wealth of its steamboat and railroad heyday left behind grand homes, churches, and commercial buildings, many of which still line the streets around Snake Alley.

The neighborhood above the alley, known as Heritage Hill, is a district of well-kept Victorian-era houses that repays a walk. From the top of the bluff the land falls away toward the broad Mississippi, and the whole area gives a strong sense of a prosperous river city built into difficult, dramatic terrain.

Most visitors experience Snake Alley on foot, climbing or descending its switchbacks and pausing at the curves to take in the old brick and the view. It is steep enough that the tilted paving is genuinely slick when wet or icy, so sure footing matters, especially in cold or rainy weather.

It is possible to drive down the one-way street, a slow and careful maneuver that gives a real feel for how tight the turns are, and cyclists have long tested themselves against the climb in an annual race up the alley. However you take it, it is a short, memorable stop on a river town full of character.

Spring and summer are the easiest seasons to visit, with warm weather and dry brick underfoot and the surrounding gardens and old homes at their best. It is a fine time to combine the alley with a stroll of the historic hill and a look at the riverfront below.

Fall brings color to the bluff and cooler days for the climb, and it is when the alley's cycling race traditionally draws crowds. Winter can leave the steep brick icy and treacherous, so it is worth extra caution, though the bare trees open up the views down toward the Mississippi.

The closest Boutel™ stays, so you can turn this stop into an overnight. Each is an independently owned, editorially selected place to stay.