Destination Main Streets

Old Town (Chicago), Illinois

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The Old Town neighborhood is the next community we will vist heading north along Lake Michigan just past the Gold Coast area. But the area wasn't always referred to as Old Town. It was originally referred to as The Cabbage Patch when German immigrants moved to the area in the nineteenth century and farmed the land. Most of the buildings were destroyed during the Great Chicago Fire of 1871. One of the few survivors was St. Michael's Church, which is today considered a major landmark in the community. Eventually, the area was renamed North Town. But people also referred to the area as Old Town in names such as the Old Town Triangle Association (Clark Street to the east being a diagonal street forming part of the triangle) and soon Old Town became the official name. Today, Old Town is filled with pubs, restaurants, shops, and boutiques. You'll also find plenty of nightlife, including several theaters and comedy clubs, such as the Second City Comedy Club, which launched the improv style of comedy as seen on Saturday Night Live and SCTV and also launched the careers of numerous comedians such as Bill Murray, John Belushi, Tina Fey, Chris Farley, and Keegan-Michael Key, just to name a few.

Wells Street is the Main Street of the Old Town area of Chicago between Division Street to the south and Lincoln Avenue to the north. The heart of the area would be the intersection of Wells Street and North Avenue. Old Town can be reached by taking the CTA Red Line subway north from the downtown Loop area and getting off at the Clark/Division stop. After exiting the subway, walk west two blocks to Wells Street, then north on Wells. Other communities in Chicago with a Main Street feel worth checking out include Lincoln Park, which is within walking distance just to the north by way of Lincoln Avenue. Or you could go to the Gold Coast neighborhood to the south. To get there on foot, head south on Wells Street, turn left on Division Street, and then turn right on State Street. Other areas worth checking out in Chicago include Michigan Avenue, Wicker Park, and Andersonville.

Photo Gallery

We start our tour of Chicago's Old Town at the intersection of Wells Street and Division Street.  Wells Street is the Main Street for the Old Town neighborhood.  Also, to get here, we traveled by foot just a few blocks west on Division Street from the intersection of State Street and Division Street, which was the northern tip of the Gold Coast neighborhood also featured on this site.
We start our tour of Chicago's Old Town at the intersection of Wells Street and Division Street. Wells Street is the Main Street for the Old Town neighborhood. Also, to get here, we traveled by foot just a few blocks west on Division Street from the intersection of State Street and Division Street, which was the northern tip of the Gold Coast neighborhood also featured on this site.
We pull back a bit and get a wider shot of Wells Street to see various residential structures with commercial on the ground floor, including a Starbucks at the corner of Wells Street and Scott Street.  In the background you can see the Chicago skyline rising up in the clouds.
We pull back a bit and get a wider shot of Wells Street to see various residential structures with commercial on the ground floor, including a Starbucks at the corner of Wells Street and Scott Street. In the background you can see the Chicago skyline rising up in the clouds.
A variety of shops and services fill these historic buildings, some with more modern touches.  Theses businesses even offer services for the locals, including gyms and dentist offices.
A variety of shops and services fill these historic buildings, some with more modern touches. Theses businesses even offer services for the locals, including gyms and dentist offices.
Comprised of nearly 30 interconnected structures built between 1880 and 1965, Cobbler Square Loft Apartments was formerly a Dr. Scholl's factory. The unique complex was converted to apartments in the mid-1980s and was renovated in 2009.  Today, Cobbler Square features a mix use of apartments, shops, restaurants, and businesses.  This is the corner of Wells Street and Evergreen Avenue.
Comprised of nearly 30 interconnected structures built between 1880 and 1965, Cobbler Square Loft Apartments was formerly a Dr. Scholl's factory. The unique complex was converted to apartments in the mid-1980s and was renovated in 2009. Today, Cobbler Square features a mix use of apartments, shops, restaurants, and businesses. This is the corner of Wells Street and Evergreen Avenue.
Across Wells Street are more shops, inlcuding a boutique, a barber shop, a bicycle shop, and a pub.
Across Wells Street are more shops, inlcuding a boutique, a barber shop, a bicycle shop, and a pub.
Here's a front view of Cobbler Square.  From this angle, you get a good view of its unique architecture.  Also, you can see one of the smoke stacks still rising in the background on the right-side of the picture.
Here's a front view of Cobbler Square. From this angle, you get a good view of its unique architecture. Also, you can see one of the smoke stacks still rising in the background on the right-side of the picture.
And across Wells Street, shoppers stroll along or just sit and rest their tired feet.
And across Wells Street, shoppers stroll along or just sit and rest their tired feet.
A pair of shoppers walk into a jewelry store.  The store on the right is called Judy Maxwell Home and is owned by Chicagoland native, Joan Cusack.
A pair of shoppers walk into a jewelry store. The store on the right is called Judy Maxwell Home and is owned by Chicagoland native, Joan Cusack.
Here's yet another view of Cobbler Square.  Yes, it basically takes up the entire block.  This time we're looking at it from the intersection of Wells Street and Schiller Street.  The Pier 1 Imports is no longer there, by the way.
Here's yet another view of Cobbler Square. Yes, it basically takes up the entire block. This time we're looking at it from the intersection of Wells Street and Schiller Street. The Pier 1 Imports is no longer there, by the way.
This is the view across the street on the east side of Wells Street.  Basically, this is the southeast corner of Wells Street and Schiller Street.  Across the street, Cobbler Square takes up pretty much the whole block.  Here you get another view of the Judy Maxwell Home store owned by Joan Cusack.
This is the view across the street on the east side of Wells Street. Basically, this is the southeast corner of Wells Street and Schiller Street. Across the street, Cobbler Square takes up pretty much the whole block. Here you get another view of the Judy Maxwell Home store owned by Joan Cusack.
On the northeast corner of Wells Street an Schiller Street is this Italian restaurant.  In the background, you can see high-rise residential towers.  Although farther from downtown Chicago (or the Loop, as it is known), you'll still find high-rise apartments and condos in this area, usually built along the shore of Lake Michigan.
On the northeast corner of Wells Street an Schiller Street is this Italian restaurant. In the background, you can see high-rise residential towers. Although farther from downtown Chicago (or the Loop, as it is known), you'll still find high-rise apartments and condos in this area, usually built along the shore of Lake Michigan.
The Old Town Pour House is a huge restaurant and bar in the heart of Old Town.  When I was taking pictures of the area, this trolley was parked for awhile out front.  Must be a pretty popular spot?  I did see some ads later for Trolley Pub Crawls so this could be for one of them.
The Old Town Pour House is a huge restaurant and bar in the heart of Old Town. When I was taking pictures of the area, this trolley was parked for awhile out front. Must be a pretty popular spot? I did see some ads later for Trolley Pub Crawls so this could be for one of them.
We head a little further north on Wells Street and find some more businesses.  Some of these, as you can see, are services that cater to the local community, such as nails and haircuts, but there are some shops and cafes throughout.
We head a little further north on Wells Street and find some more businesses. Some of these, as you can see, are services that cater to the local community, such as nails and haircuts, but there are some shops and cafes throughout.
A lady walks past a piece of public art while across the street historic properties are being renovated for new tenants.
A lady walks past a piece of public art while across the street historic properties are being renovated for new tenants.
And we can look back on that same stretch from across the street.  Behind the art installation is a paved plaza containing gardens and residences.  This is part of the West Burton Place apartments, a series of Victorian homes that were joined together and formed into eclectic apartments featuring unique architectural touches.
And we can look back on that same stretch from across the street. Behind the art installation is a paved plaza containing gardens and residences. This is part of the West Burton Place apartments, a series of Victorian homes that were joined together and formed into eclectic apartments featuring unique architectural touches.
Across the street, are several restaurants with a wide variety of architecture and each featuring outdoor seating.  The Spice House was established in 1957, so it's been around awhile.  Meanwhile the Benchmark has a more modern look to it.
Across the street, are several restaurants with a wide variety of architecture and each featuring outdoor seating. The Spice House was established in 1957, so it's been around awhile. Meanwhile the Benchmark has a more modern look to it.
Another view of the same stretch of businesses.  This gives you an idea of the wide variety of dining options you can find in Old Town along with the variety of architecture in the area.
Another view of the same stretch of businesses. This gives you an idea of the wide variety of dining options you can find in Old Town along with the variety of architecture in the area.
Here's a view looking northbound and across the street on Wells Street.  High-rise residential towers can be seen in the distance.  The higher floors have good views of Lake Michigan just to the east.
Here's a view looking northbound and across the street on Wells Street. High-rise residential towers can be seen in the distance. The higher floors have good views of Lake Michigan just to the east.
Across the street is a fudge shop, a hot dog shop, and an aquarium, each housed in some interesting architecture, especially that hot dog shop in the middle with that glass work on the second and third floors.
Across the street is a fudge shop, a hot dog shop, and an aquarium, each housed in some interesting architecture, especially that hot dog shop in the middle with that glass work on the second and third floors.
Crossing back over again (we've been zigzagging up Wells Street here), we see another restaurant and a familiar chain.  Ivy climbs up that historic rowhome on the left.
Crossing back over again (we've been zigzagging up Wells Street here), we see another restaurant and a familiar chain. Ivy climbs up that historic rowhome on the left.
We go back to the other side of Wells Street again as we make our way north.  Here we get another view of the Old Town Aquarium, which opened in 1975.  Just goes to show how long some of these businesses have been around and how resilient the area has been.
We go back to the other side of Wells Street again as we make our way north. Here we get another view of the Old Town Aquarium, which opened in 1975. Just goes to show how long some of these businesses have been around and how resilient the area has been.
Across the street, a shopper walks up from a resale boutique on the bottom floor of a split-level.  Upstairs is a barber shop.  In the distance is a bagel shop.  Notice the light posts throughout the area?  A nice touch for this stretch.
Across the street, a shopper walks up from a resale boutique on the bottom floor of a split-level. Upstairs is a barber shop. In the distance is a bagel shop. Notice the light posts throughout the area? A nice touch for this stretch.
Here's a view looking back southbound along the east side of Wells Street in the direction we had just come from.
Here's a view looking back southbound along the east side of Wells Street in the direction we had just come from.
And here's a view looking northbound at the west side of Wells Street.  Zanies is one of several comedy clubs in the area.  Old Town is known for its nightlife, not just its pubs but also its theaters and shows.
And here's a view looking northbound at the west side of Wells Street. Zanies is one of several comedy clubs in the area. Old Town is known for its nightlife, not just its pubs but also its theaters and shows.
This is another view of that same stretch.  Up Down Cigar opened in 1963, again just to give you an idea of the longevity of some of the businesses along this stretch.
This is another view of that same stretch. Up Down Cigar opened in 1963, again just to give you an idea of the longevity of some of the businesses along this stretch.
Here's a view of the southeast corner of Wells Street and North Avenue.  On the right side of the picture you can see one of the many Old Town Gates.  These are installed all along Wells Street.
Here's a view of the southeast corner of Wells Street and North Avenue. On the right side of the picture you can see one of the many Old Town Gates. These are installed all along Wells Street.
Here's a better view of the Old Town Gates that are so prevalent along this stretch of Wells Street.  You can just walk right under them while strolling through Old Town.
Here's a better view of the Old Town Gates that are so prevalent along this stretch of Wells Street. You can just walk right under them while strolling through Old Town.
This is a view of the northeast corner of North Avenue and Wells Street.  North Avenue is a major east-west highway running through the area.  The high-rises in the background overlook Lincoln Park—the actual park (not the community), which borders Lake Michigan, just to the east.
This is a view of the northeast corner of North Avenue and Wells Street. North Avenue is a major east-west highway running through the area. The high-rises in the background overlook Lincoln Park—the actual park (not the community), which borders Lake Michigan, just to the east.
If we turn left and head west on North Avenue we get this view of Pipers Alley, a complex of shops that also includes the Second City Comedy Club.  Second City launched the improv style of comedy as seen on Saturday Night Live and SCTV and also launched the careers of numerous comedians such as Bill Murray, John Belushi, Tina Fey, Chris Farley, and Keegan-Michael Key.
If we turn left and head west on North Avenue we get this view of Pipers Alley, a complex of shops that also includes the Second City Comedy Club. Second City launched the improv style of comedy as seen on Saturday Night Live and SCTV and also launched the careers of numerous comedians such as Bill Murray, John Belushi, Tina Fey, Chris Farley, and Keegan-Michael Key.
Here's a view looking east along North Avenue back towards Wells Street.  Across the street you can see the Old Town Ale House, which opened in 1958.
Here's a view looking east along North Avenue back towards Wells Street. Across the street you can see the Old Town Ale House, which opened in 1958.
We head back to Wells Street.  This is a view of the west side of Wells Street looking southbound.  Fleet Street Sports is connected to Pipers Alley.  You can see another sign for Second City in the background.
We head back to Wells Street. This is a view of the west side of Wells Street looking southbound. Fleet Street Sports is connected to Pipers Alley. You can see another sign for Second City in the background.
Across the street and slightly further north are more shops, boutiques, and some neighborhood services such as cleaners.
Across the street and slightly further north are more shops, boutiques, and some neighborhood services such as cleaners.
And going back across the street again, we have some more shops and businesses, this time in a more modern style building.
And going back across the street again, we have some more shops and businesses, this time in a more modern style building.
This is a view of the southeast corner of Wells Street and Eugene Street.  The area north of North Avenue is referred to as the Old Town Triangle.
This is a view of the southeast corner of Wells Street and Eugene Street. The area north of North Avenue is referred to as the Old Town Triangle.
Boutiques can be found along this stretch of Wells Street.
Boutiques can be found along this stretch of Wells Street.
A shopper heads south past a coffee shop along the stretch of Wells Street we just came from.
A shopper heads south past a coffee shop along the stretch of Wells Street we just came from.
Here's another view, this one also looking southbound along Wells Street.  The businesses get a bit more sparse here as we begin to leave the main commercial hub of Old Town.
Here's another view, this one also looking southbound along Wells Street. The businesses get a bit more sparse here as we begin to leave the main commercial hub of Old Town.
At the northern tip of Wells Street is the Hotel Lincoln, a recently renovated historic hotel right on Lincoln Park.  This is the far northern border of the Old Town neighborhood and the southern end of the Lincoln Park neighborhood.  From here, we turn right on Lincoln Avenue.  You can check out our Lincoln Park gallery on this site as well.
At the northern tip of Wells Street is the Hotel Lincoln, a recently renovated historic hotel right on Lincoln Park. This is the far northern border of the Old Town neighborhood and the southern end of the Lincoln Park neighborhood. From here, we turn right on Lincoln Avenue. You can check out our Lincoln Park gallery on this site as well.

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