A Day Trip to Oswego
The Port City is rich in history — and plenty of different foods
By Chris Clemens
Any leaf peeper knows the trees in New York start to turn soonest in the Adirondacks.
From there colors creep outward in all directions until eventually the Empire State is a gorgeous landscape of yellows, reds and oranges.
Oswego isn’t in the Aidrondacks — but because of its proximity, you’ll typically see changing colors here a little sooner than you might in regions further south.
This fall get a head start on your foliage tour and checkout the Port City of Central New York.
As a port city, Oswego’s shipping history goes back centuries. This stop-off in Lake Ontario meant merchant ships could deliver goods to regions in New York that weren’t otherwise as accessible from ports in New York City. As a result, the city’s relationship to the shipping industry and its maritime culture runs deep.
The H. Lee White Maritime Museum sits properly on the edge of the water and offers a glimpse into the long history of Oswego’s shipping industry. Here at the museum, you can also take a boat ride, about one mile, out to the historic West Pierhead Lighthouse, known locally as the Oswego Lighthouse. For many years the lighthouse wasn’t open to the public. But now it’s one of the most unique tours you’ll find in the region.
The city’s position on the water didn’t just give it a legup with commerce, but also with national security. The stories of U.S. military battles fought on these shores are retold through historical exhibits at Fort Ontario State Park. The star-shaped fort is now a New York state historic site and offers an opportunity to walk through an important piece of the state’s history. Visitors to the park might also be surprised to learn that the land adjacent was the site of the only place in the country to house Jewish refugees during World War II. The Safe Haven Museum is walking distance from the fort and tells the story of those brought here from other countries seeking refuge and safety. Even the most casual of history buffs will appreciate that there’s no other place like it in the country.
The water systems in Oswego haven’t just been used for commerce and war. There’s also a burgeoning recreational boating scene here. Marinas on the lake give locals access to the Great Lakes. Plus, visitors by boat can step off the dock and be walking distance to the downtown area.
In 2023, Oswego became the first city in the state to complete its Downtown Revitalization Initiative. Years earlier the Governor’s office in Albany awarded a number of improvement grants to different municipalities and each set out to use those funds to reinvent their communities.
Oswego’s efforts gained special recognition for not only completing the projects sooner than other cities, but for creating improvements that impact visitors in addition to the local residents. While you’re completing your tour of the water’s edge, be sure to visit the new River Walk. The modern upgrades to the public park really give visitors an opportunity to view Lake Ontario in ways you won’t find in other parts of the state.
The Downtown Revitalization Initiative also gave the city a shot at revitalizing their city center. A brand new Water Street Pocket Park — between Water Street and West First Street — now hosts regular live music events and a chance to sit and enjoy the city. The park is surrounded by views of downtown that blend historic legacy and modern upgrades.
Anyone who has been to Oswego in the past and is revisiting now will likely catch themselves noting how much has changed in this section of the city.
The construction of buildings like the Litatro right on the river have given the landscape a fresh makeover. On the top floor of Litatro you’ll find the Rooftop Lounge with fine dining and a view of the city like no other restaurant can offer. A few doors up, the Red Sun Fire Roasting Co. provides a more casual atmosphere with an elevated menu highlighting its wood-fired oven.
For a super casual breakfast, Wade’s Diner is a veteran gem on the eastside featuring classic diner favorites like eggs and pancakes. Locals know the food here is fantastic, but they also know the quirky history with this spot. The original diner was housed in a Pullman train car when it opened in 1937. When Neal Wade purchased the train car to open his diner, he hadn’t gotten a proper permit to bring it into town. Instead of dealing with the bureaucratic red tape of procuring a permit, he and a few friends moved the car into place in the middle of the night when no one was paying attention. The next day everyone couldn’t believe their eyes when a Pullman train car was sitting at the side of the road and no one could (or would) explain how it got there. With no evidence of how it arrived, there was no scapegoat to issue a ticket to. History was made with the founding of Wade’s and since then the survival of a fire, multiple owners and nearly a century of great food they’re still continuing to make history.
If you’re just looking for a quick snack, Oswego has also been incredibly supportive to small businesses with a niche offering. Heidi Ho Donuts just up the road from Wade’s is a small woman-owned bakery that offers doughnuts that go way above and beyond. River Walk Coffee Roasters is just a few doors up from the pocket park and its own coffee roasts bring a big-city specialty coffee flare to the small urban community here.
Further west near SUNY Oswego is Rudy’s, which is practically famous for its hot dog and fries style menu. Plus, any Oswego local will tell you that the shoreline next to Rudy’s is the best place in all of Lake Ontario to catch a sunset.
Whether it’s a small specialty doughnut shop or high-end rooftop dining, there’s a wide range of offerings in Oswego that will appeal to any palate. With museums, waterside recreation, festivals and plenty more, Oswego has plenty of reasons to visit.
Chris Clemens was born, raised and still lives in Rochester. With a penchant for exploring his own backyard, he has used words and digital media to tell the stories of Upstate New York that he’s discovered on the road.