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A Local’s Guide to the Perfect Weekend in St. Charles, Missouri

A Local’s Guide to the Perfect Weekend in St. Charles, Missouri

Whether you are visiting from out of town, a local or looking for a St. Louis getaway, a weekend in St. Charles, Missouri is a MUST! This city has so much charm and history that you are going to fall in love with this city as I have. I might be slightly biased because St. Charles is Adam’s hometown and as a couple, we have enjoyed several great weekends in St. Charles.

There are so many diverse things to do in St. Charles – from outdoor adventures to casual walks on Main Street with a refresh of American history. Furthermore, once springtime hits, you can easily find a fun festival to attend almost every weekend in St. Charles.

So with that said, please enjoy my local guide (thanks to Adam) of the perfect weekend in St. Charles Missouri.

A couple hanging out of a four pedal bike on a red-brick sidewalk.

Full disclaimer –  We were invited by St. Charles Convention and Visitors Bureau to feature the city. As always, our opinions are non-biased and our own. Our post may contain affiliate links. When you click on the link you will have the option to purchase a product at no extra cost to you, but we would receive a small commission. We want to thank everyone for following and supporting us on all of “Our Sweet Adventures.” 

How to Get Around for a Weekend in St. Charles

For both visitors and locals, a great way to get around and enjoy some of the best things to do in St. Charles is by the St. Charles Trolley or Uber.

A red and green trolley in St. Charles on Main Street.

The St. Charles trolley operates from April to December and is FREE for everyone! From start to finish it is a 30 minute loop around some of St. Charles best attractions. There are 11 stops which include the St. Charles Convention Center, Ameristar Casino Resort Spa, Streets of St. Charles, Frenchtown, Mark Twain Village and 5 stops along Main Street. It is a very easy and convenient way to travel in St. Charles.

Uber has been around for a few years, but just arrived in St. Charles. If you are unfamiliar with Uber, it is a reliable taxi service where you can share rides with others or request a private ride as an alternative to traditional taxi cabs. The fares are always shown to you up front and are usually a fair price. It is a fast and easy way to get around St. Charles because you can request a driver from the Uber app at any time – any day.

Friday Night and the Feeling’s Right

What better way to start your weekend in St. Charles than with fun games, craft beers, and maybe a little gambling too!

Two Plumbers Brewery + Arcade

I cannot think of a better start to a weekend in St. Charles than this awesome microbrewery with ALL the games you can imagine! You will have to leave the children under 21 years old behind to enjoy classic board and arcade games. When I say Two Plumbers Brewery + Arcade has ALL the games you can imagine, I am not exaggerating. I lost count after 50. I like to think of myself as a board game lover, but I had never heard of half of these board games before. They have classic cards and board games such as The Game of Life, Battleship, Clue, Guess Who?, UNO, Boggle, Risk, Monopoly, Operation in addition to some fantasy/science fiction ones. So grab a friend, a table and a craft beer and enjoy!

A dark room with people playing classic pinball machines at Two Plumbers Arcade and Brewery.

If cards and board games are not your thing, don’t worry, Two Plumbers also has several different classic arcade games and pinball machines. To name a few of my favorites are Time Crisis 2, The Simpsons, Frogger, Ms. Pacman, and Galaga. Most of the games are only 25 cents, and if you are anything like my brother-in-law, you might beat an entire game with less than five dollars.

In addition to all the fun games, what makes Two Plumbers Brewery + Arcade special, is the other half of their name – brewery. They are a microbrewery creating some of the best beers in the state! On tap, you will find their latest featured beers which are always on rotation in addition to other craft brewery beers from Missouri and around the nation. To cap it off, they also serve delicious street food. Needless to say, you have everything you need to spend all night at Two Plumbers Brewery + Arcade.

Ameristar Casino Resort Spa

For games with a little more money on the line, visit Ameristar Casino Resort Spa. The St. Charles Ameristar has one of the largest casino floors in the country boasting 130,000 square feet. You can place your lucky bet on slot machines, video poker, table games, baccarat or in the poker room.

Furthermore, going to Ameristar has been one of the local’s favorite things to do in St. Charles because it’s a little getaway within the city. In addition to the casino, Ameristar also features a hotel, relaxing spa, delicious dining options, luxury retail shops, and a night scene with bars and a night club. It is a little slice of Las Vegas within St. Charles.

Saturday’s on Main Street

Some of the best things to do in St. Charles is in the historic district, more commonly referred to as Main Street. Main Street is 14 blocks long and runs parallel to the Katy Trail and Missouri River. The beautiful red-brick-paved streets are filled with charming buildings dating back to the early 1800s. Today, these buildings have been fully restored and are now local retail shops, restaurants, and more.

A couple holding hands running across  red-brick road in St. Charles.

We love Main Street so much, we could spend every weekend here! Whether it is to go shopping, eat delicious food, or simply enjoy a nice walk – a weekend in St. Charles is not complete without a visit to Main Street. So with that said, let me show you how to have the best day on Main Street!

Read next: The Best Things to Do in St. Louis with Toddlers

Bike Stop Cafe

Bike Stop Cafe is the perfect spot to start your day on Main Street because every day needs to start off with a hearty meal. Their breakfast and lunch menu is heavily focused on healthy options using organic produce which includes their greens, drip coffee, espresso, and tea. Some of the menu options include salad, soup, sandwiches, wraps, quesadillas, and more. In addition, the cafe is located along the Missouri River and Katy Trail so you can enjoy your breakfast inside the cute shop or outside on the patio with views of the Missouri River.

Must order: White Rabbit Latte, Triathlon Wrap, and Jodi’s Famous (Chocolate) Peanut Butter Balls.

In addition to delicious and healthy entrees, Bike Stop Cafe is also known for their bike rentals, service, and equipment. So if you enjoy biking, this is a great place to rent a bike and explore the Katy Trail. They even offer a shuttle service along the Katy Trail. Or if you are looking for a great family endeavor, you can rent their 2 or 4 seat pedal cars to bike on Main Street.

Shopping on Main Street

One of the best things to do in St. Charles is to simply walk on Main Street – so make sure you are wearing your best comfy travel shoes! The smell of the fresh air, green trees towering over the red-brick-street, and the beautiful historical buildings create a lovely atmosphere. With that said, it will take you a while to walk all 14 blocks quickly because every cute shop is going to tempt you to walk inside.

Main Street has all the shops you could ever imagine. From clothing stores to gourmet foods, little knick-knacks, and more. A few favorite shops I enjoy are Olde Town Spice Shoppe, Main Street Marketplace, and Di Olivas. Old Town Spice Shoppe has all the spices you need to perfectly season your dishes at home. Main Street Marketplace is the cutest building stocked with several tasty sampling dips, mustards, and sauces as well as jams, coffee, decorative accessories, gifts, and more. Di Olivas is the perfect store to find the most unique flavor infused olive oil and balsamic vinegar such as Smokey Chipotle Olive Oil and Cinnamon Pear Balsamic Vinegar. As you can see, after one walk on Main Street you will leave with your hands full of goodies for your next meal.

Little Hills Winery Wine Shop

Calling all wine enthusiasts, you cannot miss this shop on Main Street! Little Hills Winery is the only winery in the city of St. Charles and has some of the best wines I have ever had. The winery was founded in 1998 and has evolved into an award-winning winery producing between 16 and 20 different wines per year. You cannot tour the winery, but you can visit their wine shop on Main Street. To find out which wine you should walk away with, enjoy one of their wine tastings where you get to choose which wines to taste.

A wine glass filled with wine focused with four bottles of wine from Little Hills Winery in the background.

I did their wine tasting and enjoyed Little Hills Traminette, Ada Tyler’s Harvest Peach, Mead, and Chocolate Strawberry. Each wine was delicious, but my two favorites are the Traminette and Ada Tyler’s Harvest Peach. Traminette is a lovely table white wine for lunch or dinner while Ada Tyler’s Harvest Peach is a wonderful semi-sweet wine to end a meal. If you are looking for something truly unique, the Chocolate Strawberry tastes EXACTLY like you are enjoying a chocolate covered strawberry! To top this amazing wine tasting off, with the tastings of at least four wines, you walk away with a complimentary Little Hills Winery souvenir glass.

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Grandma’s Cookies

To continue your sweet adventure on Main Street, head to Grandma’s Cookies – a store not only known locally but around the world! Grandma’s Cookies history dates back to 1976 and has been making people smile ever since with her famous homemade cookies.

A white cookie jar labeled Grandma's Cookies with a stack of four cookies to the right of the jar.

The cookies are your classic flavors baked to perfection – Chocolate Chip, Peanut Butter Chocolate Chip, Snickerdoodle, Oatmeal Raisin, Sugar Sprinkles and a few more. Each cookie is soft, thick, and oh so delicious! If baked cookies are not your thing, Grandma’s Cookies also serves cookie dough too! The simplicity of this old-timey bakery and its long history in the city is what truly makes Grandma’s Cookies special and a great treat.

Sugar Cubed

Of course, this website is called, “Our Sweet Adventures” for a reason and I could not pass up the opportunity to step inside Sugar Cubed. Sugar Cubed is St. Charles own little Willy Wonky world. It is full of nostalgic candies and chocolates that will satisfy any sweet tooth. They have over 800 different types of candies from local to novelty, nostalgic, gourmet, and international all in either bulk or package. Furthermore, they even have an Alchemy Soda Bar that serves unique treats like gourmet cotton candy, soft serve ice cream, fresh popcorn, house roasted nuts, craft sodas, candy mocktails, locally roasted Course Coffee, and more! Talk about a “sweet adventure!”

Lewis and Clark Boat House and Museum

St. Charles, Missouri is rich in history. It is the first permanent European settlement on the Missouri River and the starting point of Lewis and Clark’s greatest expedition. Therefore, you will see touches of Lewis and Clark throughout the city such as the Lewis and Clark Restaurant, monument and the Boat House and Museum.

A statue of Lewis and Clark monument surrounded by trees and bushes in St. Charles

The Lewis and Clark Boat House Museum is a nice quaint museum dedicated to the famous explorers. There is a beautiful diorama highlighting the expedition from start to finish, a display of their campsite, a video room showcasing the historical journey and more. Moreover, one of the most impressive pieces of the museum is the scale-model boats. For most of the year, you will find them in the boathouse under the museum but if you are lucky, you can find them in the water during special events or re-enactments.

Big A’s on the Riverfront

Almost every time we visit St. Charles over a weekend, you will find us at Big A’s hanging out with friends. Big A’s on the Riverfront is the best place to grab drinks, wings, and hamburgers with friends on a Saturday night on Main Street. The atmosphere is live and friendly. You are treated like family and everything is laid back and relaxing. It is like St. Charles very own Cheers but with hardcore Cardinals and Blues fans.

Four friends smiling for a photo and toasting with shot glasses at Big A's.

Lazy Sundays

After a full day on Main Street, enjoy your Sunday relaxing with one more fun attraction during your weekend in St. Charles before you head home.

Fast Lane Classic Cars

Regardless if you love cars as much as I do not, you must visit Fast Lane Classic Cars during your weekend in St. Charles. It is truly one of the best things to do in St. Charles and it is FREE! Fast Lane Classic Cars is a family-owned classic and collector car dealership with three showrooms filled with over 180 classic cars, trucks, and motorcycles. These showrooms are open to the public to walk around and marvel at all the pristine cars on display. Furthermore, if you love any of them, you can BUY the cars on display! Or if you are like me, you can just dream of owning one some day.

Fast Lane Classic Cars does a wonderful job restoring each classic car, truck and motorcycle into a lovely piece of art ready to be on the road again. I had the BEST time walking in each showroom appreciating the beauty surrounding me. I saw several beautiful Shelby Cobra convertibles, a 1920s car that looked like it belonged in the Great Gatsby, a pink Cadillac and so many more fantastic cars. Again, you cannot miss out on Fast Lane Classic Cars!

Where to Eat in St. Charles

St. Charles has so many amazing restaurants to enjoy. Since they are so close to St. Louis they have some of the same “must eat” dishes like St. Louis style ribs and thin crust pizza, custard, toasted ravioli, and gooey butter cake. After a weekend in St. Charles, I always leave feeling happy and full because of all the delicious food. In addition to a few places already mentioned, here are a few of my favorite places.

Pio’s Restaurant

Pio’s Restaurant is an Italian restaurant just a few blocks from Main Street that has been serving lunch and dinner since 1958. They have delicious food using recipes from Pio’s mother raised in Modena, Italy and a friendly atmosphere that welcomes you with open arms. As briefly stated, St. Louis is known for their thin crust pizza and toasted ravioli and Pio’s was the first to introduce both phenomenons to the St. Charles area. Furthermore, this is where Adam worked through high school, so Pio’s is like family to us – but I am sure we are not the only ones who feel this way. It is truly one of the most historical eating establishments in St. Charles. We never leave St. Charles without enjoying toasted ravioli and St. Louis style pizza from Pio’s Restaurant and neither should you!

A platter filled with toasted ravioli and a small cup of marinara sauce in the middle from Pio's Restaurant.

Must order: Toasted Ravioli with Meat Sauce, Pio’s Special Pizza (pepperoni, sausage, mushrooms, onions, and green pepper), Prime Rib, and Fried Chicken.

Sugarfire Smokehouse

Sugarfire Smokehouse is a signature BBQ restaurant in the St. Louis area with locations in St. Charles as well. As a born and raised Texan where we eat, sleep, and breathe BBQ, let me put on record this place is AMAZING! I am not the only one who feels this way. They have been named Best Barbecue by the Travel Channel, St. Louis Magazine, Feast Magazine, won awards at the Memphis in May World Barbecue Championships and World Food Championship, featured on Pitmasters, Beat Bobby Flay, and Burgers, Brew, and Que, and The New York Times. So yes, it is amazing!

You cannot go wrong with anything you order, but the St. Louis baby back ribs, beef brisket, and speciality sandwiches are all mouthwatering and delicious. They also serve vegetarian options, scrumptious sides, sweet desserts, and boozy milkshakes. Needless to say, do not miss out on Sugarfire Smokehouse BBQ during your weekend in St. Charles

Must order: St. Louis baby back ribs, Big Muddy, Baked Beans, Sugarfire Pie, and Smoked Sea Salt Chocolate Chip Cookies.


St. Charles has one of the best pastry shops in the Midwest that is a force to be reckoned with. The owners Agi and Aaron Groff create artisan baked goods (including gluten-free) made with local, seasonal, and natural ingredients. With a strong European influence, they have meshed their European-style with an American taste to create exquisite pastries. They use unique flavors to bake European pastries such as orange and lavender olive oil cake, frangipane tart, canele (French pastry), and French macarons to American favorites like cheesecake, brownies, and of course, gooey butter cake. So whether you are looking for something new to try or want something traditional, Sucrose has every sweet thing you need.

A variety of European and American desserts (macarons, apple pie, chocolate cake, and truffles) from Sucrose bakery in St. Charles, MO.

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Lyons Frozen Custard

A St. Charles staple is Lyons Frozen Custard. Adam will surely tell you that you cannot leave St. Charles without enjoying Lyons Frozen Custard. If you are unfamiliar with custard, it is a more smooth and dense frozen dessert with more egg yolks and less air incorporated than regular ice cream. Lyons Frozen Custard has been a familyowned business churning custard for over 30 years. In addition to custard, they also serve snow cones, sundaes, shakes, and old-fashioned sodas but the real treat is the frozen custard. You are bound to find you favorite flavor because they have countless different flavors including Cookie Dough (Adam’s favorite), Mint, Oreo Cookie, Reese’s Pieces, and many more.

A cup full of Lyon's frozen custard with a spoon dipping into it.

I hope my guide on a weekend in St. Charles has been helpful and inspirational to planning your own trip. It is truly a hidden gem of the Midwest and a great city you will fall in love with. From their rich history to brick-roads, buildings from the 1800s, wine tastings, craft beers, sweet treats, delicious food, classic cars, games, and more – you can see there are so many wonderful things to do in St. Charles. It is truly a perfect city for a little getaway for everyone!

For any further information to help plan your weekend in St. Charles, please visit St. Charles visitor website.

JORD Hyde - a Timeless Watch for Travel + Giveaway

Thursday 25th of July 2019

[…] one reason we love JORD watches is that they are founded and made in St. Louis, Missouri – Adam’s hometown. Moreover, every JORD wooden watch is inspired by nature and made with all-natural wood and the […]

Steve Powell

Sunday 19th of May 2019

Have you ever stayed overnight in the St. Charles Historic District at one of the Inns? Check out Boone's Colonial Inn sometime.


Tuesday 4th of June 2019

I have not because we always stay with family, but maybe next time we will. We have heard nothing but wonderful things about Boone's Colonial Inn. Thank you for the recommendation.


Sunday 19th of May 2019

I was so NOT expecting to see a post from St. Charles when I was scrolling through the FTB FB group! I'm also from St. Chuck, and you've done a great job showcasing it. :)


Tuesday 4th of June 2019

Haha I was not expecting someone from FTB to recognize St. Charles! Thank you so much for your kind words. Maybe you know my husband's family since it's such a small city :)

Vaisakhi Mishra

Saturday 18th of May 2019

Sucrose knows how to get you addicted to sugar! <3 Also, St Charles is such a quaint town!! You made me fall in love with the place :D


Tuesday 4th of June 2019

Yes, they do! And aww that just made my day. I hope you get the chance to visit soon. It is a wonderful city.


Friday 17th of May 2019

Oh wow, what a lovely looking place. Talk about a blast from the past kind of trip. All that food looks amazing, and I can't decide what I want more - the cookies or the ravioli!


Tuesday 4th of June 2019

You must get both! The toasted ravioli is amazing!!! It is definitely something you must try before leaving St. Charles and St. Louis areas. The cookies are also delicious :) I hope you get the chance to visit St. Charles soon - it is a wonderful city.