Chesapeake on Main Launches New Dining Offerings
Submitted photo
Hand-pressed burgers served at Chesapeake on Main.
Gabe Stark
The Trenton Telegraph
The Trenton Telegraph is pleased to have Chesapeake on Main as one of the first businesses to partner with the Telegraph to launch our community perks program, which aims to keep news and businesses local.
When you subscribe to the Trenton Telegraph, you’re doing more than just staying informed – you’re investing in the future of our community. Now, with our Community Insider Perks program, that investment goes even further.
With exclusive discounts and offers from local businesses, your subscription can easily pay for itself. Whether it’s saving a few dollars on dinner, getting a deal on home services, or picking up something special at a neighborhood shop, Insider Perks puts money right back into your pocket.
With this partnership, subscribers of the Telegraph can enjoy a half pound burger with fries and a drink for just 10 dollars at Chesapeake on Main.
A fresh wave of flavor and community spirit has arrived in downtown Trenton, Missouri, with the opening of Chesapeake on Main, a restaurant that’s already making waves for its unique blend of East Coast seafood tradition and Midwestern comfort food.
Owner and chef, Jason Kephart, who originally is from Maryland’s Chesapeake Bay, brings a lifetime of seafood experience to Trenton.
“Some of these recipes are family heirlooms, and our approach to seafood is all about freshness and authenticity,” Kephart said. “I want people to have an experience, not just a meal.”

Submitted photo
Fried Fish and Shrimp served at Chesapeake on Main.
Chesapeake’s menu is designed to offer something for everyone. While the weekends are reserved for signature seafood and steakhouse fare, the restaurant is launching a new dining schedule to cater to local tastes and talents. Starting December 7, the restaurant will operate with two distinct teams and offerings throughout the week.
“We’re rolling out a new concept,” Kephart said. “Our Sunday, Monday, and Tuesday service will feature classic comfort foods and local favorites, thanks to some fantastic new staff. Thursday, Friday, and Saturday will remain dedicated to our seafood and steak specialties. We’ll be closed on Wednesdays to get ready to go again on the weekend.”
The change is a response to both customer feedback and the arrival of experienced local cooks, including Jerry Saw, a well-known figure in the Trenton dining scene.
“Jerry used to run the Wild Onion and worked at Washington Street—people have followed her food for years,” the Kephart said. “Now she’ll be bringing her flavors to our comfort food nights, while we continue our seafood focus on the weekends.”
The owner’s philosophy is rooted in customer experience.
“I care about people first. I want them to enjoy themselves, and I work day and night to figure that out. Most businesses put profit margins first; for us, that’s secondary to making it work for everybody.”
Chesapeake on Main is also positioning itself as a gathering place for the community. The dining room features a variety of seating options, from high-tops to booths, with plans for laptop-friendly tables and a laid-back atmosphere.
“We want this to be a space where people can come together, hang out, do homework, watch sports, or just enjoy good food and conversation,” Kephart said.
As the restaurant adapts to Trenton’s unique rhythms and demographics, the message from Chesapeake on Main is clear: “
Just be patient. It’s something new for us and for the community, and we’re all headed for the same goal.”
With fresh seafood delivered within days from the coast, hand-pattied never-frozen burgers made with local Missouri beef, and a secret batter for their signature fried dishes, Chesapeake on Main is offering Trenton a new dining experience, one that’s as much about connection as it is about cuisine.

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