The Oregon Trail Through Ashtabula, Ohio

Ashtabula

On the shores of Lake Erie, 18 miles from the Pennsylvania border, Ashtabula (pop. 18,079) is a large and busy port, first dredged at the mouth of the Ashtabula River in 1826 and later home to some of the biggest shipyards on the Great Lakes. Now primarily recreation-oriented, Ashtabula still has more than a few signs of its industrial past, including the massive coal conveyor that forms an archway over the river, next to a squat lighthouse and a small local history museum housed in the old lighthouse keeper’s quarters. Pride of place goes to a burly bascule drawbridge over the Ashtabula River. The many turn-of-the-20th-century industrial buildings along Bridge Street form a three-block parade of gift shops, bars, and restaurants.

The town’s lakeside location made it a key transit point for enslaved people escaping on the Underground Railroad, a history recounted inside the Hubbard House Museum (1603 Walnut Blvd., 440/964-8168, Fri.-Sun. afternoons Memorial Day-Labor Day, $5).

One last local landmark is a half mile south of the harbor: Tony’s Dog House (528 Lake Ave., 440/964-0202), a friendly indoor-outdoor hangout serving well-prepared all-beef dog with a huge variety of toppings, plus delicate ribbon-fried potatoes and soft-serve cones.

Conneaut

The eighteen miles between Ashtabula and the Pennsylvania border offer a full range of Great Lakes scenery, from pristine waterfront forests and lakeside vacation cabins to historic covered bridges and massive power plants, best seen by following Lake Road, which runs right along the shore. Close to the state line, the historic town of Conneaut (pop. 12,567, pronounced “KAH-nee-ot”) is home to an engineering landmark, the 136-foot-long Middle Road Covered Bridge, built in the 1860s and restored in the 1980s, five miles south of downtown. It also has an art director’s dream of a road-food restaurant, the White Turkey Drive-In (388 E. Main Rd., 440/593-2209), on US-20. Owned and run by the Tuttle family since 1952, this place serves burgers and has a fantastic ambience but is truly famous for shredded turkey sandwiches, root beer floats, and chili-cheese fries. Between Mother’s Day and Labor Day, sit outside under the red canopy on a warm summer evening watching the fireflies, and everything is guaranteed to feel right with the world.