15 Best Things to Do in Greenwood (IN)

Just beyond the south side of Indianapolis, Greenwood is a city that has grown at an astonishing rate since the 1990s.

In that time the population has more than doubled, to 60,000, a large portion of which is from the last ten years alone.

That growth has gone hand-in-hand with spectacular investment in the city’s parks and public amenities, making Greenwood a colorful place to be in summer.

The historic center, known as Old Town Greenwood, dates back almost 200 years, and is also in the process of a remarkable regeneration, complementing a string of shopping centers, entertainment amenities and the Greenwood Park Mall along U.S. Route 31.

1. Craig Park

The largest public space in the old heart of Greenwood is a place for people to gather during the summer.

At the end of June you’ve got the Freedom Festival, and then in mid-August WAMMFest, brings Wine, Art, Music and Microbrews for a heady mix of culture, food and drink.

Surrounded by the city amenities like the Community Center and Public Library, Craig Park is packed with facilities like pickleball courts, softball diamond, a volleyball court, open play areas, picnic shelters and grills.

In winter the park’s scenic trails are ideal for a cross-country skiing trip.

2. Southside Art League

There’s an exciting art scene bubbling under the surface in Greenwood, anchored by this organization that has been around for six decades now.

The Southside Art League was founded in 1964, and met in properties around the city before moving into two historic buildings at 299 East Broadway St. in 1990.

A wonderful platform for local artists, the Off Broadway Gallery here is open Wednesday through Saturday, hosting themed exhibitions that are refreshed four times a year.

The Southside Art League also has an educational calling, scheduling classes in drawing, oils, watercolors, pastels, acrylics and portraiture, as well as regular workshops and demonstrations.

3. Freedom Springs Aquatics Park

One of many new public facilities in Greenwood is this extraordinary water park, offering a perfect family day out in the summer and attracting people from neighboring communities.

Freedom Springs has a 25-meter lap pool, a beach entry pool, a long lazy river and a zero-depth play area for toddlers and smaller children.

There’s also a drop slide, as well as two body slides and a tube slide, all with extra twists and turns because of their unusual height. The park also hosts a variety of special events, including live music from the central island, and regular movie screenings after sunset.

4. Old Town Historic District

At the intersection of Main Street and Madison Avenue you’ll come to the Greenwood that existed long before the recent waves of development that have swept the city.

It’s not hard to see the potential of this area, with its rows of old brick buildings, century-old houses and smattering of local shops, services, breweries and restaurants.

Old Town Greenwood was recently designated a Historic District, and is the setting for an open house event every November, when more than 20 businesses and buildings open their doors to the public.

When we wrote this article, the district was the focus of a revitalization project that will attract new businesses, build new homes, make extensive street improvements and create a walkable infrastructure linking this downtown area with parks and trails in the city.

5. Oaken Barrel Brewing Company

Craft beer connoisseurs are well served in Greenwood with a handful of breweries in the city and neighboring communities.

One that deserves special mention is the Oaken Barrel Brewing Company, which has been in business since 1994, making it the second-oldest brewpub in the state.

Oaken Barrel continues to be a must-visit, garnering the critic’s choice award from Indianapolis Monthly for “Best Brewpub in Indy”.

There’s a family section, an outdoor dining section and a banquet facility. The flagship brews are Indiana Amber (Red Ale), Gnaw Bone (Pale Ale), Razz-Wheat (Fruit Beer), Superfly (IPA), Snake Pit (Porter) and Alabaster (Wheat Beer).

The food menu is New American, and popular picks include mesquite-smoked ribs and Cajun jambalaya pasta.

6. Old City Park

Old City Park, Greenwood — Old City Park

At the time of writing, this community park by Old Town Greenwood had just been given a multimillion-dollar overhaul.

Most striking of all is the futuristic playground, centered on a unique, 20-foot tower, made up of three cubes stacked at juxtaposing angles.

This is surrounded by other new play features, all on safe astro turf surfaces. Among the other details are a custom climbing net, foosball table and a flowing open space for non-structured developmental play.

Old City Park is on the banks of Pleasant Creek, and another excellent new addition is an 18-foot-wide promenade next to the water.

7. Greenwood Amphitheater

In a picture perfect spot at the north end of Craig Park, by Pleasant Creek, is Greenwood’s main venue for public outdoor events.

With a wooded backdrop and lush lawns, the Greenwood Amphitheater hosts the ever-popular Summer Concert Series.

These shows take place on Saturday evenings, June through August. You can bring a lawn chair, blanket and cooler, for a diverse feast of live music, often accompanied by vendors from local restaurants and craft breweries.

This is also the setting for events during Greenwood’s Freedom Festival in late June, as well as festive light show at Christmas.

8. Greenwood Park Mall

Running through the center of Greenwood there’s a sequence of shopping centers and big box stores along U.S. Route 31.

Foremost of these is the Greenwood Park Mall, which has been here in some form since 1967.

Now operated by Simon Property Group, the mall has witnessed a lot of change in the last 50+ years, starting out as an open air mall before being enclosed in 1980 and given an upscale redesign in the 2000s.

There are close to 150 stores and services here, and a few of the many familiar names are Macy’s, JCPenney, Sephora, Barnes & Noble, Old Navy, GameStop, American Eagle and Forever 21.

Food-wise you’ve got Cheesecake Factory, T.G.I. Friday’s, Chick-fil-A and Mall mainstays like Wetzel’s Pretzels, Auntie Anne’s, Sarku Japan and Charleys Philly Steaks.

9. Rascal’s Fun Zone

If you need ideas for restless kids there’s a family entertainment center a few minutes south of Greenwood in Whiteland.

Rascal’s Fun Zone has indoor and outdoor go-karts (two tracks each), two 18-hole mini-golf courses, bumper board equipped with water cannons, indoor bumper cars, ten lanes of mini- bowling and a large arcade with new releases and redemption games, all accompanied by a fast food stand.

You can save money with a variety of all-access wristband packages, for the whole day or 1-3 hours of continuous fun.

Height requirements apply to the go-karts, bumper cars and bumper boats, and all attraction and game token sales stop 30 minutes before closing.

10. Southport Antique Mall

For close to 30 years, a rather nondescript old warehouse close by in Southport, has concealed a labyrinthine multi-dealer antiques center.

The Southport Antique Mall is far larger than it appears from the outside, with 30,000 square feet of floor space home to dozens of vendors.

In fact you will need a map to navigate this place. Give yourself as much time as you can on your hunt for collectibles, shabby chic pieces, upcycled items and antiques ranging from Indiana glassware to furniture, books, fashion, accessories, fabrics, vinyl, pottery, clocks and so much more.

11. Mallow Run Winery

This winery in nearby Bargersville is named for a stream that runs through the property. The surrounding 600-acre farm grows corn and soybeans, but since 2000 a significant patch has been devoted to grapes.

The vineyard now covers 12 acres and the winery followed in 2005, converting a rustic timber-frame barn from the 19th century into a cozy tasting room.

With something for all palates, Mallow Run’s range includes varietals like Sauvignon Blanc, Traminette, Chardonnay, Cabernet Sauvignon, Marechal Foch and Syrah, as well blends and fruit wines.

The winery is open daily, with extended hours on Saturdays from Memorial Day to late September. Throughout the summer there’s a picnic concert series, and you can attend a slew of special experiences all year, from craft fairs to yoga + wine.

12. Regal Greenwood & RPX

Right next to Greenwood Park Mall is the city’s only movie theater. This 14-screen megaplex opened in 2000 and was the last cinema in the Indianapolis area to be built by the now defunct General Cinemas brand.

Regal took over a few years later, and the cinema remains a go-to for family outings, movies with friends and date nights.

In contrast to many multiplexes, all of the screens are big and spacious, with reclining seats, cup holders, ample leg room and a high level of cleanliness throughout.

Check the listings for regular classic movie screenings amongst the new releases.

13. Hickory Stick Golf Club

With an Irish links layout, this public track in Greenwood resembles no other course in Indiana.

Hickory Stick Golf Club has recently picked up awards from the Indiana Golf Course Owners Association, and was one of four finalists for the 2020 National Course of the Year.

What you get here is a tough but playable challenge, with rolling, bent grass fairways, mounded rough and fast and true greens. You’ll need to factor the wind into your shot selection, while water is a feature on nine holes.

14. Smock Golf Course

Another fine option for golfers is this publicly owned, daily fee course on the north side of Greenwood.

An 18-hole, par 72, Smock Golf Course is rated as one of the best in the Indianapolis area for newcomers, thanks to its choice of tee boxes and forgiving layout.

This is also a great place to brush up on your game, with PGA staff available for lessons, an excellent driving range and chipping and putting areas.

The clubhouse has a fully-stocked pro shop, and a bar & grill if you need to recharge after your round.

15. Greenwood Farmers’ Market

With vast tracts of farmland on three sides of Greenwood, you can be sure that this city has a flourishing farmers’ market.

Held on Saturday mornings at 525 N Madison Avenue, May through September, the market has grown steadily over the last 30+ years, and is a weekly ritual for many residents.

The Greenwood Farmers’ Market is one of the most convenient ways to support local businesses while shopping for produce, ingredients and food from the people who grow, make and prepare them.

The selection changes as the summer progresses, from plants early in the season to corn and apples as fall approaches.

On a normal week you can expect to find fruit and vegetables, organic meat, artisanal soaps, honey eggs, salsas, jams, fresh baked bread, pastries and kettle corn.