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Weekend Getaway in Indianapolis: The Complete Itinerary

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4 months ago

Situated in the center of the Hoosier State, Indianapolis represents one of the major destinations for events in the Midwest. The Circle City successfully blends the big city amenities you’d expect in Chicago or New York with the friendlier feel of a smaller city. In this Indianapolis getaway weekend itinerary, you’ll have plenty to do in Indianapolis, without feeling like you’re getting lost in the shuffle.

Whether you’re coming in to see the big race or you’re simply looking for some Hoosier Hospitality, you’ll find several reasons to visit Indianapolis again and again. Here are a few of the best ways to spend a weekend getaway in Indianapolis, Indiana’s state capital.

When is the best time of year to visit Indianapolis?

The answer to when is the best time to visit Indianapolis depends on your reason for visiting. The city hosts college basketball’s Final Four once every five years in March, and the world-famous Indianapolis 500 automobile race takes place on the Sunday before Memorial Day in late May. If you want to enjoy one of these events in person, you’ll need to plan your trip for those periods.

For the best weather, the best time to visit is between June and September. The city is at its warmest, and outdoor activities such as White River State Park are plentiful. If you’re interested in Indiana’s foliage just south of the city, you’ll want to wait until October.

Where to Stay in Indianapolis

The hotel that dominates the skyline in Indianapolis also serves as one of the best places to stay. The JW Marriott Indianapolis was built when Indianapolis hosted the Super Bowl, and it’s still one of the top hotels in the city. You quite literally can’t miss this building with its gleaming blue glass windows visible on all sides of the city, and spectacular panorama views of the entire city.

To make sure sure that you’re in the best position for your Indianapolis getaway weekend, we recommend you stay around Mile Square. Indianapolis’s downtown is pleasantly walkable, with many of the great things to do in the city. For a quintessentially Indianapolis experience at an incredible price, we highly recommend Ironworks.

Getting to Indianapolis

Because of its location in the center of Indiana, reaching Indianapolis by car couldn’t be easier. Four different interstates carry drivers into Indianapolis, making it an easy drive from Chicago, Detroit, Columbus, Cincinnati, Peoria, Louisville and St. Louis.

All major U.S. airlines fly into Indianapolis International Airport, and if you have an extra day or two, you can even take a train into the city from Chicago, New York or Washington. The easiest way to get around Indianapolis is by car, so if you’re flying in, you should definitely rent a car from Indianapolis airport.

Top Things to See in Indianapolis

Indianapolis Motor Speedway and Museum

Even if you’re not a car enthusiast, the Indianapolis Motor Speedway and Museum is worth a visit. By seating capacity, this is the largest venue in the world, as it holds 257,325 people at capacity. The famous 2.5-mile oval track has existed since 1909, and visitors can enjoy races beyond the Indianapolis 500. The Museum is currently closed for renovations but will reopen in April 2025.

If you’re not up for watching a race, when it reopens, you can still check out the track and its museum by taking a tour of the grounds. You can even take a lap around the track yourself and perform the time-honored tradition of kissing the bricks as you cross the finish line. No word on whether or not you’ll have to bring your own milk.

Cycle the Cultural Trail and the Monon Trail

Indianapolis’s official nickname is Circle City, but it probably could be called Cycle City. The city has 59 bike trails, and its crown jewels are at the center of the city in the Indianapolis Cultural Trail and the Monon Trail.

The Cultural Trail hits some of the biggest spots in downtown Indianapolis, including White River State Park, Gainbridge Fieldhouse, Circle Center Mall and Lugar Plaza. You’ll see pieces of art and history along with the city skyline as you ride through the center of Indianapolis.

Didn’t bring a bike? No worries: the city’s NBA team, the Indiana Pacers, sponsors a rideshare program that sets up bicycles for rent at multiple locations. If you ride through the Arts and Theater District on Massachusetts Avenue, known to locals as Mass Ave, you’ll end at Bottleworks which has Indy’s newest food hall at The Garage.

Indianapolis has a surprising array of interesting foods, so get yourself on the best tour of the food scene for some unexpected flavors.

If you really want some exercise, you can go north on the Monon Trail toward Carmel. This trail covers 24 miles by bike and leads you into some of the well-to-do northern suburbs of Indianapolis. It’s a great way to enjoy some natural beauty as you head north out of the city.

Visit Monument Circle and the War Memorial Plaza

Did you know that Indianapolis boasts the second-highest total of war memorials in the United States, behind only Washington? At the center of it all and the center of the city is Monument Circle, which features the Soldiers and Sailors Monument to all Hoosiers who lost their lives defending the United States in its first 125 years as a nation. The best walking tour of the city includes a stop at the Monument.

The Monument really becomes a sight during the late winter months, as Indianapolis hangs lights from it and turns it into its version of a Christmas tree. The buildings around the circle offer a fun show for visitors as well, as the city uses the surrounding buildings for a nightly light show.

War Memorial Plaza features the Indiana World War Memorial and Museum as well as 25 acres’ worth of monuments and memorials. If you’re a student of history, you’ll want to include this on your Indianapolis getaway weekend itinerary.

The best way to visit: Go! Running Tours

Travel Insighter brings you the best insights – and the best insights come through locals. Go! Running Tours has recently released a very comprehensive tour of Indianapolis with Reena, a local guide who knows the best of Indy’s five cultural districts.

The running tour is the perfect whirlwind tour of everything from Mass Ave to the City Market. If you want to cover a lot of ground in the Circle City – and quickly – then this is the perfect tour for you.

For the kids: The Children’s Museum

If you’re bringing kids on your Indianapolis getaway weekend, a stop by the Children’s Museum is absolutely the right choice. There’s a whole range of indoor and outdoor exhibits to keep even the most picky of kids entertained, and the Indy Attraction Pass (make sure you buy it in advance!) includes the Museum and the White River State Park.

Best Places to Eat in Indianapolis

Being in the crossroads of North America means Indianapolis has access to some of the best food the Midwest has to offer. Here are a few of the places you really can’t miss while you’re in Indy. We recommend that you let the locals take the reins in a food tour of Massachusetts Avenue which also includes a stop through the Murat Theatre at the Old National Centre.

St. Elmo Steak House

This steakhouse has been an Indianapolis institution for more than a century. St. Elmo Steak House has sat downtown since 1902 and offers some of the best steaks you’ll find anywhere in the Midwest. The other reason diners flock to St. Elmo is the famous shrimp cocktail. Indy locals will tell you that an Indianapolis getaway weekend itinerary just isn’t complete without a stop at St. Elmo Steak House.

The joke in Indianapolis is, if you like the people you’re dining with, you tell them about the horseradish before they take a bite. If you don’t like them, you tell them after.

Be warned: the heat from the horseradish is intense, but the flavor from the shrimp and sauce are worth it. If you really can’t stomach anything spicy, you can ask for a milder version.

Cake Bake Shop

Some of the prettiest and best-tasting cakes can be found at The Cake Bake Shop in Broad Ripple and in Carmel. Gwendolyn Rogers uses only fresh, seasonal ingredients in her beautiful cakes, and the restaurant looks like you’ve stepped into a royal tea party.

The cakes are expensive, but they’re big enough to share and incredibly decadent. Cake Bake Shop is also a great place to go for a fancy brunch with family and friends; just be sure to save room for dessert.


Indiana’s huge pork tenderloins can be found in many locations, and Mug’n’Bun is one of the best. Enjoy a perfectly fried pork tenderloin, pounded thin and coming off the bun. Pair it with a mug of root beer and you have a true taste of Indianapolis.

It’s an old-school drive-in that locals know and love, but you can drive up and park or eat at the tales. The menu is gloriously extensive and inexpensive, and they make their own root beer (including diet root beer). This is an easy stop on your Indianapolis getaway weekend itinerary that we suspect will be one of your best memories of the city.

Where to Shop in Indianapolis

The Fashion Mall at Keystone is the place to go if you’re looking for upscale shopping. It’s a bit difficult to reach, as it’s on the northwest side of the city, but it’s well worth the drive because it’s home to some of the biggest brands available in Indianapolis.

For downtown shopping, the local stores on Mass Ave and the Circle Centre Mall offer plenty of stores to satisfy every interest.

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