Highland, Indiana

Exploring Highland, Indiana: A Three-Day Weekend Itinerary

Welcome to Highland, Indiana – a charming town located just 30 minutes south of Chicago. Nestled in Lake County, this hidden gem offers a delightful mix of natural beauty, historical landmarks, and a vibrant local scene. Join us on a three-day adventure as we uncover the best attractions, restaurants, and sights this enchanting town has to offer.

Day 1: Discovering Highland’s Natural Beauty

Morning: Wicker Memorial Park

Start your day at Wicker Memorial Park, a sprawling 139-acre park that offers a variety of recreational activities. Take a leisurely stroll along the picturesque trails surrounded by lush greenery, or rent a bike to explore further. Don’t miss the tranquil Japanese Gardens, perfect for some peaceful reflection. Afterward, head to the Wicker Memorial Park Golf Course for a few rounds of golf amidst stunning natural surroundings.

Afternoon: Downtown Highland

After an active morning, treat yourself to a delightful lunch at a local favorite, Blue Butterfly Restaurant. This charming eatery serves up delicious American fare with a creative twist. Indulge in their signature Blue Butterfly Burger or savor the flavors of their mouthwatering seafood dishes.

Once you’re fueled up, take a leisurely stroll through Downtown Highland. This vibrant district is brimming with boutique shops, art galleries, and charming cafes. Pop into Art Gecko to admire the work of local artists and perhaps find a unique souvenir to take home.

Evening: Highland Grove

As the day winds down, head to Highland Grove for a relaxing evening amidst nature. This beautifully landscaped park offers serene walking paths, a calming pond, and plenty of benches to sit and unwind. Enjoy a picnic dinner surrounded by the sounds of nature, or simply take in the tranquil atmosphere as the sun sets.

Day 2: Immersing in History and Culture

Morning: John Dillinger Museum

Start your day by delving into the notorious history of the 1930s at the John Dillinger Museum. Located in the historic Old Lake County Courthouse in nearby Crown Point, this captivating museum showcases artifacts and exhibits that recount the life and crimes of the infamous bank robber. Explore Dillinger’s personal effects, learn about his daring escape from the Crown Point Jail, and discover the local law enforcement’s efforts to bring him to justice.

Afternoon: Hesston Steam Museum

After exploring the criminal past, embark on a unique adventure at the Hesston Steam Museum. Located just a short drive away in LaPorte, Indiana, this living museum transports you back in time with its collection of fully operational steam locomotives. Climb aboard the vintage trains and take a scenic ride through the picturesque countryside. Don’t forget to stop by the working sawmill and blacksmith shop to witness traditional craftsmanship in action.

Evening: Dinner at Langel’s Pizza

End your day with a flavorful dinner at Langel’s Pizza, a local institution known for its delicious deep-dish pies and warm hospitality. Choose from a variety of Chicago-style pizzas loaded with your favorite toppings, or opt for their mouthwatering pasta dishes. Pair your meal with a craft beer or a refreshing cocktail from their extensive drink menu.

Day 3: Outdoor Adventures and Culinary Delights

Morning: Hoosier Prairie State Nature Preserve

Immerse yourself in the natural beauty of Highland by visiting the Hoosier Prairie State Nature Preserve. This protected area boasts diverse ecosystems, including wetlands, prairies, and woodlands. Lace up your hiking boots and explore the well-maintained trails that wind through the preserve, offering stunning views of wildflowers, native wildlife, and unique plant species. Keep an eye out for migratory birds, as the preserve is part of the Lake Michigan Flyway.

Afternoon: Lunch at Maria’s Buena Cocina

After working up an appetite, head to Maria’s Buena Cocina for a delightful Mexican lunch. This family-owned restaurant is known for its authentic cuisine made with fresh ingredients and bursting with flavor. Indulge in their sizzling fajitas, homemade guacamole, and mouthwatering enchiladas. Don’t forget to pair your meal with one of their refreshing margaritas or a traditional Mexican soda.

Evening: Lake County Fairgrounds

Wrap up your Highland adventure with an evening of fun at the Lake County Fairgrounds. Check their events calendar to see if any festivals, concerts, or special events are taking place. From live music performances to exciting exhibitions, there’s always something happening at this lively venue. If there are no events scheduled, take a leisurely stroll around the fairgrounds, admiring the charming barns and enjoying the peaceful surroundings.

As your three-day weekend in Highland comes to an end, take a moment to reflect on the wonderful memories you’ve made. From tranquil parks to captivating museums and delicious dining experiences, Highland has showcased its unique charms. This small town has left a big impact, promising unforgettable adventures for those seeking a retreat from the bustling city life.

Safe travels and happy exploring!

Note: Please check attraction websites for any updated information on hours of operation and reservations.

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