Tucked between southeastern Michigan’s technical and intellectual hubs, Detroit and Ann Arbor, the town of Ypsilanti — “Ypsi,” to locals and friends — is far from New York City, my stomping grounds in the 80s and early 90s. But it’s a progressive, gritty, resurgent community with a funky attitude that improbably reminds me of Greenwich Village in the mid-1990s.
Its footprint is three times that of the Village, but it has intimate nooks for history, culture, and entertainment. Like the Village, Ypsi has a historic district that serves as a hub for social venues, local businesses, and community events. Both have restaurants, parks, and festivals. Ypsi’s embrace of counterculture reminds me of the Village before national retailers and gentrification changed the landscape there. In Ypsi in 2026, midwestern dynamics and sensibilities give the town a spacious, relaxed aura that embraces the unique and defies the mainstream.
© Destination Ann Arbor
Grub Hub – Depot Town
Growing up in NYC, I’m no stranger to restaurant-hopping. So, during my first visit in the mid 1990s to explore the local food co-op in Depot Town, I was intrigued by the turn-of-the-century architecture around Cross Street, which serves as a backdrop for a variety of culinary options.
Sidetrack – A Stalwart of History
The home of the Ypsilanti Train Depot, which opened in the 1830s, Depot Town now hosts community stalwarts and newer enterprises. Sidetrack became my summer go-to spot for mega strawberry shortcake that can feed four diners, if you stick to the FDA’s recommended serving amounts. Beyond the restaurant’s extensive selection of appetizers, burgers, and sandwiches, there’s a spirit of resilience. Sidetrack has survived a 1929 train derailment and Prohibition, has been recognized by GQ magazine for its burgers, and has served as a filming location for the film Conviction starring Hilary Swank. But as a local legend, it’s the scene of generations of family outings, birthday parties, and seasonal holiday celebrations.
Thompson & Co/Mash – Contemporary Options
Kitty-corner from Sidetrack stands an 1860s building that served as barracks for Civil War enlistees (including the First Michigan Colored Infantry), and is home to two newer dining options. Thompson & Co is a lunch/dinner and weekend brunch spot. With high ceilings and expansive windows that surround the dining area, the open space is an ideal setting for reimagined southern dishes and comfort foods.
During summer festivals, my favorite pastime is enjoying pear fig pizza or shrimp & grits on the elevated deck, which is ideal for people-watching. Mash, their whiskey bar, is an after-five weekend venue; it’s a favorite place to decompress in supple lounge chairs, with a variety of libations and elevated food options such as charcuterie, Louisiana shrimp, and mini beignets. Live music makes Mash a year-round hot spot, but for me, the vibe heats up in the summer with patio seating where I enjoy watching trains speed through Depot Town.
Proud of Ypsi Pride
Whether you choose Sidetrack, Thompson & Co, or Mash, all three venues are just steps from several annual festivals. For me, the summer season means Ypsi Pride in July. An experience reminiscent of sweltering days in NYC, weaving through crowds, Ypsi Pride is a fashion show/dance party/advocacy expo where the alternative is the norm.
At my first Pride celebration, families and students intermingled with drag queens and furries. People-watching is a welcome break from exploring the festival vendors. A performance stage in the middle of Cross Street, fronted by a dance space, feels like Washington Square Park, a favorite Village locale. But unlike NYC, Ypsi revelers can choose between nearby Frog Island Park’s unpaved walking track or Riverside Park’s Huron River views for casual strolls.
The Michigan Avenue Scene
While Depot Town is a major hub for Ypsi activities, Michigan Avenue (midway between Interstate 94 and Depot Town) is the official downtown, with a more contemporary feel. A 10- to 15-minute walk from Depot Town, it’s home to office buildings, business incubators, and a University of Michigan ambulatory health care facility that reinforces its mainstream vibe. But there are pockets of buzz.
Encuentro – Gateway to South America
Among several dining options, Encuentro stands out. During a recent Friday evening date night, venues with liquor service were filled, so Encuentro was our sole option. The casual diner, decorated with Guatemalan art that pays homage to the cuisine, was my first exposure to pupusas (homemade corn tortillas filled with meat, cheese, or vegetables) and chirmol sauce (a smoky, tomato-based condiment used in several dishes). A downtown fixture since 2015, it’s a booze-free, affordable alternative with a loyal local clientele.
Retail Row
A few doors down, there are several retailers to intrigue shoppers. Blackstone Bookstore and Cultural Center is a local business dedicated to bringing visibility to Black literature. My standard stop for gift cards, Blackstone hosts not only author events but also educational sessions and community activities that appeal to the intellectual set.
Looking for items with a less learned feel? The Rocket is the place for a wide spectrum of goods and gifts. On Saturday afternoons, I’ve seen kids, parents, and folks of a certain age meander through narrow aisles packed with old-school candy (Now and Laters, anyone?), plush offerings, board games, novelty socks, and things that defy categorization for treasure hunters seeking the nostalgic, offbeat, or unexpected.
© Destination Ann Arbor
As a bar and retail operation, the Ypsi Cocktail Club offers not only signature drinks that change with the seasons, but also bottled, locally crafted spirits, including Ypsi gin, vodka, and whiskey. Club patrons can also select from a range of flights and pours, but I’m particularly impressed with their range of mocktails that can be enjoyed in a subdued atmosphere.
While Ypsi offers a variety of experiences beyond Depot Town and Michigan Avenue, these are the places that take me back, at least a bit, to my time of growth and experimentation in the Village. As the community and I continue to evolve, Ypsi supports evolution that visitors can embrace.
If You Go
Ypsi’s right off of Interstate 94, between Ann Arbor and the Detroit Metropolitan Airport. Curb and off-street parking are available.
- Accommodations in Ypsi include national hotel chains, bed-and-breakfasts, and apartment rentals.
- As the home of Eastern Michigan University and Washtenaw Community College, Ypsi has a strong student presence.
- Visit Ypsi Real for the latest on area events and activities.
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