The Oregon Trail


Auburn (pop. 26,454) is a proud industrial city with a solid, hilly downtown and a rich stock of historical homes, including that of William H. Seward, the antislavery Whig governor of New York. Seward founded the Republican Party, was a U.S. senator, served as secretary of state under presidents Abraham Lincoln and Andrew Johnson, and single-handedly negotiated the purchase of Alaska from Russia in 1867. The Seward House Museum (33 South St., 315/252-1283, 10am-5pm Tues.-Sat., Sun. summer, $14), on Hwy-34 two blocks south of US-20, contains all the original furniture and many fascinating historic exhibits.

Down the street from the Seward home, you can also tour the home of the heroine of the Underground Railroad, Harriet Tubman, who lived here from before the Civil War until her death in 1913. The tidy white house is now protected as part of the Harriet Tubman National Historical Park (180 South St., 315/882-8060, Tues.-Sat., donation). In 1859, William Seward, then a U.S. senator, quietly sold Harriet Tubman the home for almost no money, which was both generous and illegal, and he and Tubman are both buried in the town’s Fort Hill cemetery, west of South Street between their two homes.

Right downtown, the sparkling streamlined Hunter’s Dinerant (18 Genesee St., 315/255-2282, daily), a 1950s O’Mahony, offers great greasy-spoon breakfasts, thick slices of pie, and a panoramic view of the aging Genesee Beer sign that watches over the wide streets of the hill-hugging downtown.


Roughly midway across New York State, Skaneateles (pop. 2,463, pronounced “scan-ee-AT-less”) is a pristine sun-dappled resort nestled on the north shore of shimmering Skaneateles Lake. This popular summer family escape houses arts, crafts, and antiques stores along its immaculate Genesee Street (US-20), which fronts a lovely lakeside park where you can enjoy free summer concerts (around 7:30pm, Fri.) on the quaint bandstand, watch the boats come and go, or hop on board a historic lake steamer for a scenic tour offered by Mid-Lakes Navigation (11 Jordan St., 800/545-4318 or 315/685-8500).

Stroll up the main downtown north-south drag and you’ll notice the smell of fresh bread (and delicious doughnuts!) at the unadorned Skaneateles Bakery (19 Jordan St., 315/685-3538) before reaching the Skaneateles Historical Society’s Museum at the Creamery (315/685-1360, Fri.-Sun. July-Aug. and late-Nov.-Dec., donation). Elm-lined side streets are full of well-maintained Greek Revival homes.

If you’re hungry for more than a pastry or piece of cake, wait in line at the high-quality but self-effacing Doug’s Fish Fry (8 Jordan St., 315/685-3288, daily), “Not Famous since 1982,” for its lobster rolls, fried clams, seafood chowder, and ice-cold beer. Doug’s also has creamy thick Perry’s ice cream and milkshakes, plus fresh strawberry sundaes in season. Buy a postcard for a nickel and Doug’s will slap on a stamp and send it on its way.

Right in the center of Skaneateles, the Sherwood Inn (26 W. Genesee St., 800/374-3796 or 315/685-3405, $200 and up) along US-20 has been welcoming travelers to its lakeside restaurant, good bar, and comfortable rooms since it was built as a stagecoach stop back in 1807.

New York Maps

Map of the Oregon Trail through Pennsylvania and Upstate New York.
Map of the Oregon Trail through Pennsylvania and Upstate New York.
Map of the Oregon Trail through Eastern New York.
Map of the Oregon Trail through Eastern New York.

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