All Around the Town Guidebook
My Favorite Food Spots in Town
The 'My Favorite Food Spots in Town' portion of this guide will be dedicated to local restaurants unique to chesterton that I LOVE
This Mom and Pop, family-friendly diner is an all time favorite for locals! This is a Chesterton staple that offers yummy, home style meals that are filling and wholesome. It is a perfect location and allows for you to see the downtown while dining. Check out their cool wall fully covered in license plates from all over the states! Their staff is pretty awesome as well!
P.s. If you happen to visit during Taylor's shift be sure to mention Reina and Angelique sent you!
6 locals raden deze aan
Peggy Sue's Diner
117 S Calumet RdThis Mom and Pop, family-friendly diner is an all time favorite for locals! This is a Chesterton staple that offers yummy, home style meals that are filling and wholesome. It is a perfect location and allows for you to see the downtown while dining. Check out their cool wall fully covered in license plates from all over the states! Their staff is pretty awesome as well!
P.s. If you happen to visit during Taylor's shift be sure to mention Reina and Angelique sent you!
Although our town is pretty quiet at night, in the mornings everyone seems to flood into this diner! Located downtown and just a short walk away you will run into 50s inspired, Northside Diner. Always busy and always good! Everyone loves this spot for a good breakfast or lunch ( Hours are 7am-1pm). Reasonably priced and definitely hits the spots each time. Make sure to play a song on their Juke box before heading out!
10 locals raden deze aan
Northside Diner and Food Truck
100 N Calumet RdAlthough our town is pretty quiet at night, in the mornings everyone seems to flood into this diner! Located downtown and just a short walk away you will run into 50s inspired, Northside Diner. Always busy and always good! Everyone loves this spot for a good breakfast or lunch ( Hours are 7am-1pm). Reasonably priced and definitely hits the spots each time. Make sure to play a song on their Juke box before heading out!
Looking for a perfectly cozy cafe to sit and read a book? catch up with freinds and family? or even finish up on business? Our Red cup cafe is perfect for you! This quaint local cafe with eye catching furniture has all that you may need for your cafe adventures. Red Cup cafe offers food and beverage such as: paninis, quiches, baked goods, hot teas and coffees (other options avail.). The atmosphere of this cafe is great thanks to the staff, music and decor.
8 locals raden deze aan
Red Cup Cafe & Deli
115 BroadwayLooking for a perfectly cozy cafe to sit and read a book? catch up with freinds and family? or even finish up on business? Our Red cup cafe is perfect for you! This quaint local cafe with eye catching furniture has all that you may need for your cafe adventures. Red Cup cafe offers food and beverage such as: paninis, quiches, baked goods, hot teas and coffees (other options avail.). The atmosphere of this cafe is great thanks to the staff, music and decor.
The Port Drive In will have you leaving satified and nolstagic! This Old time drive in has lived up to the hype with the locals! The wait staff is great and helpful, the food is great,fast and reasonably priced. The experience is unmatched! Definitely a hidden Gem with Hot Dogs, Burgers, Classic Rootbeer Floats, Sandwiches, and more. Service is just as great as the food! The Port is open seasonally so make sure to call a head of time!:)
Port Drive In
419 N Calumet RdThe Port Drive In will have you leaving satified and nolstagic! This Old time drive in has lived up to the hype with the locals! The wait staff is great and helpful, the food is great,fast and reasonably priced. The experience is unmatched! Definitely a hidden Gem with Hot Dogs, Burgers, Classic Rootbeer Floats, Sandwiches, and more. Service is just as great as the food! The Port is open seasonally so make sure to call a head of time!:)
Looking for a drink with food on the side? (219) Taproom is the one, serving a decent selection of beers from 3 different breweries with a modest selection of liquors and wines. This place definitely has some yummy options when it comes to food as well! The bartenders are amazing and personable, they really want you to love your drink! They are more than willing to talk with you about your desires and will find what best works for you!
(219) Taproom
109 South 3rd StreetLooking for a drink with food on the side? (219) Taproom is the one, serving a decent selection of beers from 3 different breweries with a modest selection of liquors and wines. This place definitely has some yummy options when it comes to food as well! The bartenders are amazing and personable, they really want you to love your drink! They are more than willing to talk with you about your desires and will find what best works for you!
Our own local dive bar, great service for a great night! Cheap beer and loud music! Full of locals so there is always good conversation and recommendations to be had. Opened in 1910 and has had little to no renovations but that is the charm of the place, its been here, unotuched, forever!
Disclaimer: this is not a smoke-free bar.
Flannery's Tavern
125 S Calumet RdOur own local dive bar, great service for a great night! Cheap beer and loud music! Full of locals so there is always good conversation and recommendations to be had. Opened in 1910 and has had little to no renovations but that is the charm of the place, its been here, unotuched, forever!
Disclaimer: this is not a smoke-free bar.
Gastro 49 bar and grille is a go-to for most of us! Everything on the menu is great and you wont be dissappointed. The bar is great and is separated from the family eating area. This place is always packed, the staff is nice and the prices arent bad either!
6 locals raden deze aan
Gastro 49 Pub & Eatery
361 N Calumet RdGastro 49 bar and grille is a go-to for most of us! Everything on the menu is great and you wont be dissappointed. The bar is great and is separated from the family eating area. This place is always packed, the staff is nice and the prices arent bad either!
Lucrezia® Café
428 S Calumet RdDog Days Ice Cream Parlor
123 S Calumet RdThe best reward for a short walk away from the loft!
Nutrition Cove
219 South Calumet RoadWe love this pizza place! They have many different kinds of pizza and even has an all you can eat buffet on certain days!
Gelsosomo's Pizzeria Chesterton
371 Indian Boundary RdWe love this pizza place! They have many different kinds of pizza and even has an all you can eat buffet on certain days!
Third Coast Spice Cafe
761 Indian Boundary RdTao Chen's
532 Indian Boundary RdNamaste India
715 Plaza DrOur go to Indian food spot!
Theres nothin like these smoked ribs!!! They will send you to heaven!
19 locals raden deze aan
Wagner's Ribs
361 Wagner RdTheres nothin like these smoked ribs!!! They will send you to heaven!
My Feel Good Places
These are places that are near but maybe not in town that you can create memories as a solo traveler, traveling with your partner, or with family you’re visiting!
Named one of the top ten drive in in the United States!! It truly is wonderful and has those 80s/90s vibe!
23 locals raden deze aan
49'er Drive-in
675 N Calumet AveNamed one of the top ten drive in in the United States!! It truly is wonderful and has those 80s/90s vibe!
Lighthouse Place Premium Outlets
601 Wabash StOut door premium mall outlet!
Uptown Cafe
1400 LincolnwayA nice place to chill and get some work done!
This is always favorite of mine! Can even rack up a few playing pool!
6 locals raden deze aan
Inman's Bowling & Recreation Center
3201 Evans AveThis is always favorite of mine! Can even rack up a few playing pool!
Sk8World
3600 Scottsdale StRoller skating anyone!
FLUID Coffeebar
159 W LincolnwayVery popular coffee shop with rockstar vibes!
We truly love this place! The pumpkin or apple donuts will make you dream of them after getting a taste! You can apple or pumpkin pick and also take a look at some farm animals!
23 locals raden deze aan
County Line Boomgaard
200 S County Line RdWe truly love this place! The pumpkin or apple donuts will make you dream of them after getting a taste! You can apple or pumpkin pick and also take a look at some farm animals!
cool down with a drink or two
This indoor/ outdoor winery is a huge hit in our town! They are locally and family owned and always a good choice! Things to highlight about this winery:
Good food
Even better wine
Regularly have events such as trivia night, workshops and a bar crawl
weekly wine slushies
18 locals raden deze aan
Running Vines Winery
101 BroadwayThis indoor/ outdoor winery is a huge hit in our town! They are locally and family owned and always a good choice! Things to highlight about this winery:
Good food
Even better wine
Regularly have events such as trivia night, workshops and a bar crawl
weekly wine slushies
Franklin House
58 S Campbell StThis bar always seems to be packed and even hosts karaoke!
City/town information
Cute little town just 30 minutes over! Opportunities for a relaxed beachy vibe!
88 locals raden deze aan
New Buffalo
Cute little town just 30 minutes over! Opportunities for a relaxed beachy vibe!
Chicago
Check out our Chicago Guidebook for some Inspiration
The next town over but has LOTS to offer! cute shops and great coffee shops! good eats and depending on the season you may catch an outdoor concert or ice skating in the park!
24 locals raden deze aan
Valparaiso
The next town over but has LOTS to offer! cute shops and great coffee shops! good eats and depending on the season you may catch an outdoor concert or ice skating in the park!
Fun things for the Kiddos (or adultos!)
This is a great place for kids! with mini golfing, go'karts, batting catches, and arcade games!
22 locals raden deze aan
Zao Island
1050 Horse Prairie AveThis is a great place for kids! with mini golfing, go'karts, batting catches, and arcade games!
Fireflies Fun Zone
1505 S Calumet RdThis is an Indoor play area right down the street!
FunFlatables
52 Marks RdYour kid will ADORE this bouncey house wonderland!
This place is great for the younger kiddos, ages 0-10! They can play, use their imagination and learn new things, it is super hands-on!
14 locals raden deze aan
Bellaboo's Speel- en Ontdekkingscentrum
2800 Colorado StThis place is great for the younger kiddos, ages 0-10! They can play, use their imagination and learn new things, it is super hands-on!
This place is awesome! Have a group? want a fun date? or just you and your little one? They have space for everyone, even the little ones!
8 locals raden deze aan
Sky Zone Trampoline Park
1035 Eagle Ridge DrThis place is awesome! Have a group? want a fun date? or just you and your little one? They have space for everyone, even the little ones!
Sightseeing
Coffee Creek Park is a great walking and picturesque spot that protects a small oasis of natural habitat! When you visit you will see a 5 mile walking trail, water fountain, lovely stone formations and sidewalks, and much more! Our locals famously pick this spot for photoshoots of nature, class photos, prom and homecoming photos and more! Enjoy your day with a picnic or with a relaxing walk on the trail with as short as a 7 minute drive!
Coffee Creek Park
246 East Morgan AvenueCoffee Creek Park is a great walking and picturesque spot that protects a small oasis of natural habitat! When you visit you will see a 5 mile walking trail, water fountain, lovely stone formations and sidewalks, and much more! Our locals famously pick this spot for photoshoots of nature, class photos, prom and homecoming photos and more! Enjoy your day with a picnic or with a relaxing walk on the trail with as short as a 7 minute drive!
this is something our guests have a lot of fun with, miles and miles worth of hiking trails to visit to get your heart pumpin’!! you can also catch a view of the distant chicago skyline!
141 locals raden deze aan
Nationaal Park Indiana Dunes
1215 North State Road 49this is something our guests have a lot of fun with, miles and miles worth of hiking trails to visit to get your heart pumpin’!! you can also catch a view of the distant chicago skyline!
We love spending the day at the beach and staying to watch the stars. Sometimes we catch a few shooting stars!
12 locals raden deze aan
Porter Beach
Wabash AvenueWe love spending the day at the beach and staying to watch the stars. Sometimes we catch a few shooting stars!