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20 Restaurants Worth the Drive From Chicago

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It would take several lifetimes to eat through all of Chicago’s restaurants so it’s easy to have tunnel vision. Take a trip beyond city limits, though, and discover a new world of culinary delights. These 20 notable spots, spread across four states, are within short driving distance and well worth the time and effort. They’re among the best that the Midwest has to offer and perfect for a day trip or weekend getaway. New additions to this year’s list include Southern cooking specialist Ron’s Cajun Connection, Silver Beach Pizza in Michigan, and venerable New Glarus Brewing.

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Note: Restaurants on this map are listed geographically.

1. L’Etoile

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1 S Pinckney St
Madison, WI 53703

Wisconsin’s capitol is rife with exciting dining options. James Beard Award winner Tory Miller has had a huge hand in the city’s culinary growth, running four distinctly different restaurants. His flagship fine dining establishment, L’Etoile, is among the biggest local supporters of the farm-to-table movement. Explore a multitude of seasonal ingredients and cuisine styles with the chef’s tasting menu or order dishes a la carte. Either way, it’s an exquisite experience that’s on par with any Michelin-starred restaurant in Chicago.

2. Ardent

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1751 N Farwell Ave
Milwaukee, WI
(414) 897-7022
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No trek to Milwaukee would be complete without dining at Justin Carlisle’s gastronomic temple. The ever-changing tasting menu highlights innovative small plates that utilize Wisconsin’s finest products. Carlisle’s impressive pedigree also includes Red Light Ramen, an offshoot spawned from Ardent’s popular late-night noodle pop-up.

3. Sanford Restaurant

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1547 N Jackson St
Milwaukee, WI
(414) 276-9608
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Justin Aprahamian has made a name for himself as one of the region’s best chefs with his critically-acclaimed restaurant. His self-described ‘Modern Ethnic’ cuisine takes flavor profiles and techniques from across the globe and incorporates them into contemporary dishes. The result is stunning bites like sake-cured scallop and trout roe on strawberry wild flower gel with ginger cream; molasses-glazed quail with roasted matsutake mushrooms and mustard greens; and elk loin with bolognese cannelloni. For the adventurous, a surprise tasting menu presents seven sublime courses and removes decision-making from the equation.

4. Bryant's Cocktail Lounge

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1579 S 9th St
Milwaukee, WI
(414) 383-2620
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A vintage experience through and through, Bryant’s is Milwaukee’s oldest bar. Since 1938, guests have imbibed a countless number of unique and classic cocktails. There are more than 450 drinks available but instead of a menu, the knowledgeable bartenders help suggest something suited for each individual’s palate.

5. New Glarus Brewing Company

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2400 WI-69
New Glarus, WI 53574
(608) 527-5850
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The pride and joy of Wisconsin beer boasts an enormous 75,000-square-foot brewery that’s a two-and-a-half-hour drive from the Windy City. See what the hype is about by sampling all the brews at the facility, which is modeled after a Bavarian village. There’s no kitchen but food trucks are often stationed on site to complement the drinking. Those interested in learning more can take a self-guided tour or sign up for one of the hard hat tours every Friday. And don’t forget to bring a case or two back; New Glarus is sold exclusively in Wisconsin.

6. Mars Cheese Castle

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2800 W Frontage Rd
Kenosha, WI
(262) 859-2244
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Travelers headed up north for some outlet shopping in Kenosha or a trip to Milwaukee should not pass up an opportunity to stop at this beloved cheese institution right off Interstate 94. Bring a cooler and stock up on a variety of cheeses, meats, pastries, and beers from New Glarus Brewing. Hungry patrons can order hot items like grilled cheese sandwiches, brats, and cheese curds to enjoy in the bar area.

7. Franks Diner

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508 58th St
Kenosha, WI
(262) 657-1017
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Have breakfast and see a historical landmark all in one go at Franks Diner, a classic restaurant that’s been operating out of an old railway car for more than 80 years. Locals love the giant buttermilk pancakes and ‘Franks Garbage Plate’ of eggs, hash browns, peppers, meats, and more. Those with big appetites and no fear can take on the Red Men Challenge and attempt to finish six pounds of food in 45 minutes.

8. Gurnee Donuts

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4949 Grand Ave
Gurnee, IL
(847) 249-4757
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Located near Six Flags Great America, this family-run shop has been in operation since long before the donut trend reached the height of its popularity. Drop in early for a mouthwatering sugar rush before hitting the amusement park. The famous ube donut — only available on the weekends — is made with purple yam, a common ingredient in Filipino cuisine. These little Instagram stars are available in several varieties: With purple frosting, sugar glazing, or coconut shavings.

9. Abreo Restaurant

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515 E State St
Rockford, IL
(815) 968-9463
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Rockford doesn’t have the same dining reputation as other cities but Abreo shows that great things can come from unexpected places. Chef Paul Sletten pushes boundaries with a rotating selection of seasonal small plates that draw inspiration from all over. Dine on creative fare like duck nachos, asparagus cacio e pepe, beef rib eye elotes, and beet ricotta tart. When it’s nice outside, eat on the garden patio and pair the tapas with a drink from the extensive whisky and wine list.

10. Silver Beach Pizza

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410 Vine St
St Joseph, MI 49085
(269) 983-4743
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St. Joseph, Michigan is a ways away from the South Side but tavern-style pizza has found a home there nonetheless. Housed inside a 100-year-old train depot, Silver Beach Pizza delivers crisp and airy thin crust slices to beach-goers and just about anyone who appreciates a good pie. Best-selling combinations include The Carousel (pepperoni, sausage, ham, bell peppers, mushrooms) and the Garlic Greek (pepperoni, garlic, crushed red pepper). It’s a popular destination with locals so to avoid a long wait, make a reservation for the adults-only upper deck section. Don’t have a means of transportation? No worries. The restaurant is located right next to an Amtrak station.

11. Round Barn Winery, Distillery & Brewery

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10983 Hills Rd
Baroda, MI
(800) 716-9463
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With summer in full swing, this Michigan winery, brewery, and distillery is the place to be. Visitors enjoy libations in the tasting rooms, which are situated inside barns, and then mosey outside for an afternoon of bags, live music, and relaxation.

12. Bien Trucha

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410 W State St
Geneva, IL 60134
(630) 232-2665
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Chicago certainly isn’t lacking when it comes to tacos and that depth of options extends beyond city limits. Out west in Geneva, Mexican cuisine that rivals the best of the best can be found at the town’s most acclaimed restaurant. The namesake Bien Trucha tacos are a solid bet and come loaded with skirt steak, chorizo, roasted tomatillo salsa, and a layer of Chihuahua cheese. Other highlights include swordfish pescadillas and fresh avocado margaritas. The space is small so call ahead to be put on the wait list.

13. Journeyman Distillery

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109 Generation Dr
Three Oaks, MI
(269) 820-2050
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Jump on Interstate 94 and head east across state lines to this Michigan distillery that’s churning out barrels of artisan spirits. Whether it’s whisky and rum or vodka and gin, Journeyman prides itself on using the highest quality Midwestern grains. Guests can start with a tour to see the process in action and then visit the attached full-service restaurant, Staymaker, for flight tastings, craft cocktails, and Detroit-style pizzas.

14. The Stray Dog Bar & Grill

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245 N Whittaker St
New Buffalo, MI 49117
(269) 469-2727
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Make it through the dog days of summer at this canine-themed bar and grill in New Buffalo, Michigan. Its rooftop deck is the area’s hottest hangout, backed by a lineup of burgers, hot dogs, tacos, pizzas, sandwiches, and craft beers. After a day at the beach, it’s the ideal place to satisfy an appetite and relax with a cold pint.

15. 3 Floyds Brewery & Pub

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9750 Indiana Pkwy
Munster, IN
(219) 922-4425
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Can’t find Zombie Dust at the store? Head straight to the source. The Midwest’s most popular craft brewery is only a day trip across state lines. More than a dozen different draft selections keep the good times rolling at the brewpub, as does the surprisingly elevated food list that includes dishes like ramen, fried chicken pizza, and smoked pork loin. Then grab a case of beer or bomber for the road. On Sundays, tours are offered on a first-come, first-served basis.

16. Ron’s Cajun Connection

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897 US-6
North Utica, IL 61373
(815) 667-9855
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Chicagoans will have to travel south for this delicious Cajun cooking but they won’t have to go all the way down to Louisiana. Located right off Highway 6 in Utica,   Ron’s Cajun Connection is within driving distance of Starved Rock and definitely worth a pit stop. The menu features ‘swamp to table’ dishes such as alligator po’ boys, frog legs, fried oysters, catfish jambalaya, and more. And just like how it is in the Big Easy, they’re best enjoyed with a hurricane.

17. Black Dog Smoke & Ale House

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201 N Broadway Ave
Urbana, IL
(217) 344-9334
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University of Illinois students already know about Urbana’s glorious meat mecca but for everyone else, rest assured it’s worth a trip down south. Amish free-range turkey, polish sausages, and burnt ends that have been smoked for 24 hours are just a few of the expertly-executed ‘que options. Add an extensive craft beer list and it’s not hard to understand why patrons champ at the bit to get a seat at the small smokehouse.

18. Goose the Market

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2503 N Delaware St
Indianapolis, IN
(317) 924-4944
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Half market, half restaurant, wholly delicious. Guests can have it all at Goose the Market, home to one of the finest Italian sandwiches in the country — the Batali. After chowing down on sandwiches, soups, and gelato, peruse the shop's wine collection and head to the butcher for meats and charcuterie to take home.

19. Milktooth

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540 Virginia Ave
Indianapolis, IN
(317) 292-2280
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Brunch is having its heyday. Just ask Jonathan Brooks and his team at the Hoosier State’s most buzzed-about spot. Their modern diner is the best reason to get out of bed in the morning, offering daytime specialties that put ol’ eggs benny to shame. Bruschetta Dutch baby pancake, chilled cantaloupe soup, and grilled chicken thighs with gochugaru sauce are only a few of the selections that guests can look forward to. If that’s not enough, the restaurant’s dedicated coffee and alcohol program provides a jolt to start each day.

20. Bluebeard

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653 Virginia Ave
Indianapolis, IN
(317) 686-1580
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Indy native Kurt Vonnegut’s influence can be felt throughout charming Bluebeard. The gastropub gets its name from one of the author’s novels and adorns a converted 1924 warehouse space with antique typewriters and books. The pleasing aesthetic is matched by an assortment of farm-to-table fare, ranging from charcuterie to uni pasta, spicy dragon shrimp, swordfish nduja. Italian breads are also made in-house at the restaurant’s adjoining bakery, Amelia’s, and serve as the base for the restaurant's top-notch lunch sandwiches.

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1. L’Etoile

1 S Pinckney St, Madison, WI 53703

Wisconsin’s capitol is rife with exciting dining options. James Beard Award winner Tory Miller has had a huge hand in the city’s culinary growth, running four distinctly different restaurants. His flagship fine dining establishment, L’Etoile, is among the biggest local supporters of the farm-to-table movement. Explore a multitude of seasonal ingredients and cuisine styles with the chef’s tasting menu or order dishes a la carte. Either way, it’s an exquisite experience that’s on par with any Michelin-starred restaurant in Chicago.

1 S Pinckney St
Madison, WI 53703

2. Ardent

1751 N Farwell Ave, Milwaukee, WI

No trek to Milwaukee would be complete without dining at Justin Carlisle’s gastronomic temple. The ever-changing tasting menu highlights innovative small plates that utilize Wisconsin’s finest products. Carlisle’s impressive pedigree also includes Red Light Ramen, an offshoot spawned from Ardent’s popular late-night noodle pop-up.

1751 N Farwell Ave
Milwaukee, WI

3. Sanford Restaurant

1547 N Jackson St, Milwaukee, WI

Justin Aprahamian has made a name for himself as one of the region’s best chefs with his critically-acclaimed restaurant. His self-described ‘Modern Ethnic’ cuisine takes flavor profiles and techniques from across the globe and incorporates them into contemporary dishes. The result is stunning bites like sake-cured scallop and trout roe on strawberry wild flower gel with ginger cream; molasses-glazed quail with roasted matsutake mushrooms and mustard greens; and elk loin with bolognese cannelloni. For the adventurous, a surprise tasting menu presents seven sublime courses and removes decision-making from the equation.

1547 N Jackson St
Milwaukee, WI

4. Bryant's Cocktail Lounge

1579 S 9th St, Milwaukee, WI

A vintage experience through and through, Bryant’s is Milwaukee’s oldest bar. Since 1938, guests have imbibed a countless number of unique and classic cocktails. There are more than 450 drinks available but instead of a menu, the knowledgeable bartenders help suggest something suited for each individual’s palate.

1579 S 9th St
Milwaukee, WI

5. New Glarus Brewing Company

2400 WI-69, New Glarus, WI 53574

The pride and joy of Wisconsin beer boasts an enormous 75,000-square-foot brewery that’s a two-and-a-half-hour drive from the Windy City. See what the hype is about by sampling all the brews at the facility, which is modeled after a Bavarian village. There’s no kitchen but food trucks are often stationed on site to complement the drinking. Those interested in learning more can take a self-guided tour or sign up for one of the hard hat tours every Friday. And don’t forget to bring a case or two back; New Glarus is sold exclusively in Wisconsin.

2400 WI-69
New Glarus, WI 53574

6. Mars Cheese Castle

2800 W Frontage Rd, Kenosha, WI

Travelers headed up north for some outlet shopping in Kenosha or a trip to Milwaukee should not pass up an opportunity to stop at this beloved cheese institution right off Interstate 94. Bring a cooler and stock up on a variety of cheeses, meats, pastries, and beers from New Glarus Brewing. Hungry patrons can order hot items like grilled cheese sandwiches, brats, and cheese curds to enjoy in the bar area.

2800 W Frontage Rd
Kenosha, WI

7. Franks Diner

508 58th St, Kenosha, WI

Have breakfast and see a historical landmark all in one go at Franks Diner, a classic restaurant that’s been operating out of an old railway car for more than 80 years. Locals love the giant buttermilk pancakes and ‘Franks Garbage Plate’ of eggs, hash browns, peppers, meats, and more. Those with big appetites and no fear can take on the Red Men Challenge and attempt to finish six pounds of food in 45 minutes.

508 58th St
Kenosha, WI

8. Gurnee Donuts

4949 Grand Ave, Gurnee, IL

Located near Six Flags Great America, this family-run shop has been in operation since long before the donut trend reached the height of its popularity. Drop in early for a mouthwatering sugar rush before hitting the amusement park. The famous ube donut — only available on the weekends — is made with purple yam, a common ingredient in Filipino cuisine. These little Instagram stars are available in several varieties: With purple frosting, sugar glazing, or coconut shavings.

4949 Grand Ave
Gurnee, IL

9. Abreo Restaurant

515 E State St, Rockford, IL

Rockford doesn’t have the same dining reputation as other cities but Abreo shows that great things can come from unexpected places. Chef Paul Sletten pushes boundaries with a rotating selection of seasonal small plates that draw inspiration from all over. Dine on creative fare like duck nachos, asparagus cacio e pepe, beef rib eye elotes, and beet ricotta tart. When it’s nice outside, eat on the garden patio and pair the tapas with a drink from the extensive whisky and wine list.

515 E State St
Rockford, IL

10. Silver Beach Pizza

410 Vine St, St Joseph, MI 49085

St. Joseph, Michigan is a ways away from the South Side but tavern-style pizza has found a home there nonetheless. Housed inside a 100-year-old train depot, Silver Beach Pizza delivers crisp and airy thin crust slices to beach-goers and just about anyone who appreciates a good pie. Best-selling combinations include The Carousel (pepperoni, sausage, ham, bell peppers, mushrooms) and the Garlic Greek (pepperoni, garlic, crushed red pepper). It’s a popular destination with locals so to avoid a long wait, make a reservation for the adults-only upper deck section. Don’t have a means of transportation? No worries. The restaurant is located right next to an Amtrak station.

410 Vine St
St Joseph, MI 49085

11. Round Barn Winery, Distillery & Brewery

10983 Hills Rd, Baroda, MI

With summer in full swing, this Michigan winery, brewery, and distillery is the place to be. Visitors enjoy libations in the tasting rooms, which are situated inside barns, and then mosey outside for an afternoon of bags, live music, and relaxation.

10983 Hills Rd
Baroda, MI

12. Bien Trucha

410 W State St, Geneva, IL 60134

Chicago certainly isn’t lacking when it comes to tacos and that depth of options extends beyond city limits. Out west in Geneva, Mexican cuisine that rivals the best of the best can be found at the town’s most acclaimed restaurant. The namesake Bien Trucha tacos are a solid bet and come loaded with skirt steak, chorizo, roasted tomatillo salsa, and a layer of Chihuahua cheese. Other highlights include swordfish pescadillas and fresh avocado margaritas. The space is small so call ahead to be put on the wait list.

410 W State St
Geneva, IL 60134

13. Journeyman Distillery

109 Generation Dr, Three Oaks, MI

Jump on Interstate 94 and head east across state lines to this Michigan distillery that’s churning out barrels of artisan spirits. Whether it’s whisky and rum or vodka and gin, Journeyman prides itself on using the highest quality Midwestern grains. Guests can start with a tour to see the process in action and then visit the attached full-service restaurant, Staymaker, for flight tastings, craft cocktails, and Detroit-style pizzas.

109 Generation Dr
Three Oaks, MI

14. The Stray Dog Bar & Grill

245 N Whittaker St, New Buffalo, MI 49117

Make it through the dog days of summer at this canine-themed bar and grill in New Buffalo, Michigan. Its rooftop deck is the area’s hottest hangout, backed by a lineup of burgers, hot dogs, tacos, pizzas, sandwiches, and craft beers. After a day at the beach, it’s the ideal place to satisfy an appetite and relax with a cold pint.

245 N Whittaker St
New Buffalo, MI 49117

15. 3 Floyds Brewery & Pub

9750 Indiana Pkwy, Munster, IN

Can’t find Zombie Dust at the store? Head straight to the source. The Midwest’s most popular craft brewery is only a day trip across state lines. More than a dozen different draft selections keep the good times rolling at the brewpub, as does the surprisingly elevated food list that includes dishes like ramen, fried chicken pizza, and smoked pork loin. Then grab a case of beer or bomber for the road. On Sundays, tours are offered on a first-come, first-served basis.

9750 Indiana Pkwy
Munster, IN

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16. Ron’s Cajun Connection

897 US-6, North Utica, IL 61373

Chicagoans will have to travel south for this delicious Cajun cooking but they won’t have to go all the way down to Louisiana. Located right off Highway 6 in Utica,   Ron’s Cajun Connection is within driving distance of Starved Rock and definitely worth a pit stop. The menu features ‘swamp to table’ dishes such as alligator po’ boys, frog legs, fried oysters, catfish jambalaya, and more. And just like how it is in the Big Easy, they’re best enjoyed with a hurricane.

897 US-6
North Utica, IL 61373

17. Black Dog Smoke & Ale House

201 N Broadway Ave, Urbana, IL

University of Illinois students already know about Urbana’s glorious meat mecca but for everyone else, rest assured it’s worth a trip down south. Amish free-range turkey, polish sausages, and burnt ends that have been smoked for 24 hours are just a few of the expertly-executed ‘que options. Add an extensive craft beer list and it’s not hard to understand why patrons champ at the bit to get a seat at the small smokehouse.

201 N Broadway Ave
Urbana, IL

18. Goose the Market

2503 N Delaware St, Indianapolis, IN

Half market, half restaurant, wholly delicious. Guests can have it all at Goose the Market, home to one of the finest Italian sandwiches in the country — the Batali. After chowing down on sandwiches, soups, and gelato, peruse the shop's wine collection and head to the butcher for meats and charcuterie to take home.

2503 N Delaware St
Indianapolis, IN

19. Milktooth

540 Virginia Ave, Indianapolis, IN

Brunch is having its heyday. Just ask Jonathan Brooks and his team at the Hoosier State’s most buzzed-about spot. Their modern diner is the best reason to get out of bed in the morning, offering daytime specialties that put ol’ eggs benny to shame. Bruschetta Dutch baby pancake, chilled cantaloupe soup, and grilled chicken thighs with gochugaru sauce are only a few of the selections that guests can look forward to. If that’s not enough, the restaurant’s dedicated coffee and alcohol program provides a jolt to start each day.

540 Virginia Ave
Indianapolis, IN

20. Bluebeard

653 Virginia Ave, Indianapolis, IN

Indy native Kurt Vonnegut’s influence can be felt throughout charming Bluebeard. The gastropub gets its name from one of the author’s novels and adorns a converted 1924 warehouse space with antique typewriters and books. The pleasing aesthetic is matched by an assortment of farm-to-table fare, ranging from charcuterie to uni pasta, spicy dragon shrimp, swordfish nduja. Italian breads are also made in-house at the restaurant’s adjoining bakery, Amelia’s, and serve as the base for the restaurant's top-notch lunch sandwiches.

653 Virginia Ave
Indianapolis, IN

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