Highland Park

Day Trips

Start your day with a stroll through the charming streets of Highland Park, where you can admire the historic architecture and quaint shops. Grab a breakfast pastry and coffee at a local café to fuel your exploration. Don't forget to visit the Highland Park Historical Society to learn about the town's rich history.

After lunch, spend some time at the beautiful Port Clinton Square, where you can enjoy the park's greenery and perhaps catch a local art show. Visit the nearby Highland Park Art Center to appreciate the local art scene and engage with community artists. Wrap up your afternoon with a visit to the Ravinia Park, known for its outdoor concerts and lush gardens.

In the evening, dine at one of Highland Park's renowned restaurants, offering everything from Italian to modern American cuisine. After dinner, enjoy a leisurely walk along the lakeshore, taking in the stunning sunset views over Lake Michigan. End your night with a fun visit to a local music venue or theater for some live entertainment.

Start your morning with a visit to the beautiful and serene Ravinia Park, where you can enjoy a peaceful walk on the trails surrounded by nature. Bring binoculars to spot local wildlife, as the park is home to various bird species and other animals. Enjoy a light breakfast picnic in one of the park's designated areas, soaking in the natural beauty around you.

Afterward, head to the nearby Chicago Botanic Garden for an immersive experience in horticulture. Spend your afternoon wandering through themed gardens, such as the Japanese Garden and the Rose Garden, while learning about different plant species. Don't miss the chance to take part in a guided tour or workshop offered at the garden.

As the sun sets, consider enjoying dinner at a lakeside restaurant, where you can savor fresh seafood and regional dishes. After dinner, take a leisurely stroll along the lakefront, reflecting on your day immersed in nature. If you’re up for it, participate in a local stargazing event held at one of the parks.

Begin your culinary journey with breakfast at a local diner known for its hearty American fare. Afterward, visit the Highland Park Farmers Market, where you'll find fresh produce, artisanal goods, and local crafts. Chat with the farmers and vendors to learn more about the community's agricultural practices.

Continue your food adventure by taking a cooking class at a local culinary school, where you’ll learn to prepare a signature dish from the region. Enjoy the fruits of your labor for lunch, savoring the flavors of Highland Park in a communal setting. Visit specialty shops in the downtown area to pick up unique ingredients and snacks to take home.

For a memorable dining experience, reserve a table at a high-end restaurant celebrated for its innovative cuisine. Pair your meal with local wines or craft cocktails for a complete culinary experience. Conclude the evening with a dessert tasting at a nearby bakery that’s famous for its gourmet sweets.

Start your day at the Highland Park Art Center, where you can appreciate various exhibits showcasing local artists' work. Engage with interactive exhibits or participate in a morning art workshop to unleash your creativity. Enjoy a light breakfast at the center's café, which often features local art on display.

Visit the nearby Highland Park Public Library, which often hosts art-related events and exhibitions. Spend time exploring the library’s extensive collection or join a book club session if available. Afterward, head to the Art Institute of Chicago, which, although a short drive away, is a must-see for art enthusiasts.

For dinner, choose a restaurant that features live music or an art-themed ambiance, allowing you to dine in a creatively stimulating environment. Afterward, attend a performance at a local theater, whether it’s a play, musical, or concert, to experience the vibrant arts scene. End your evening with a nightcap at a nearby bar known for its artistic cocktails.

Kick off your day with an invigorating run or bike ride along the scenic trails at the Lake County Forest Preserves. Enjoy the lush landscapes and fresh air while you get your blood pumping. Stop by a café afterward for a refreshing smoothie or healthy breakfast to reenergize.

Spend your afternoon at a local sports facility where you can try your hand at tennis or golf, enjoying the friendly competition. Join a group class or hire an instructor for a more personalized experience. Afterward, take a break at a nearby park where you can relax or have a picnic lunch.

As the day winds down, unwind at a sports bar where you can catch a game and enjoy classic pub fare. Engage with locals to learn more about the community’s sports culture and perhaps even join in a friendly game yourself. Wrap up your day with a stroll in one of the local parks to enjoy the evening breeze.

Begin your day with a guided tour of the historic homes in Highland Park, where knowledgeable guides share fascinating stories about the architecture and families that lived there. Take your time exploring and photographing the beautifully preserved buildings. Stop for breakfast at a nearby café that offers a taste of local flavors.

After lunch, visit the Highland Park Historical Society to explore artifacts and photographs that highlight the city's rich heritage. Engage with interactive displays and learn about significant events that shaped the community. Spend the rest of your afternoon at the scenic Lighthouse Park, where you can enjoy stunning views of Lake Michigan.

For dinner, dine at a restaurant featuring historical decor that reflects the city’s past. Join a local ghost tour or historical walking tour in the evening to hear spooky tales and intriguing history. Conclude your day with a nightcap at a bar with historical significance, where you can reflect on the stories you've learned.

Start your day with a rejuvenating yoga session at a local studio, surrounded by tranquil settings that promote relaxation. Afterward, enjoy a wholesome breakfast at a health café that focuses on nutritious, locally sourced ingredients. Take some time to reflect on your wellness journey and set intentions for the day ahead.

Visit a nearby spa for an afternoon of pampering, choosing from a range of treatments such as massages, facials, or aromatherapy. Spend time in the spa’s relaxation area, taking in the serene ambiance and perhaps enjoying herbal teas. Afterward, take a leisurely walk in a local park, allowing nature to enhance your sense of peace.

For dinner, find a cozy restaurant that offers healthy yet delicious meals, perfect for nourishing your body. Attend a meditation session or wellness workshop in the evening, focusing on mindfulness and self-care techniques. End your day with a calming herbal tea or a relaxing bath at your accommodation.

Kick off your adventure-filled day with a thrilling visit to a nearby zip-lining or ropes course, where you can experience the thrill of soaring through the trees. Enjoy the adrenaline rush and scenic views that come with the experience. Afterward, refuel with a hearty breakfast at a local diner that caters to adventurers.

Next, embark on a kayaking or paddleboarding adventure on Lake Michigan, enjoying the beautiful water and surrounding scenery. Explore the shoreline and perhaps stop at a secluded beach for some relaxation. After your water activities, grab lunch at a beachside café to refuel.

For dinner, find a lively restaurant that offers a fun atmosphere and perhaps live music to celebrate your adventurous day. If you're still up for it, consider joining a local group for night hiking or stargazing at a nearby park. Cap off the evening with a bonfire, sharing stories and laughter with fellow adventure seekers.

Begin your day at the Highland Park Shopping District, where you can explore a variety of boutiques and specialty shops. Take your time browsing through unique items and perhaps picking up a souvenir or two. Stop for breakfast at a local café known for its artisanal pastries and coffee.

Afterward, visit the nearby Northbrook Court for an afternoon of shopping in a larger mall setting, offering both popular brands and luxury retailers. Enjoy lunch at one of the many eateries within the mall, sampling different cuisines. Spend some time at the mall's entertainment center, which may feature a cinema or arcade.

For your final dinner, savor a meal at a rooftop restaurant offering stunning views of the city skyline as the sun sets. After dinner, explore the nightlife options, such as wine bars or lounges, where you can enjoy music and mingling with locals. Reflect on your trip while enjoying the vibrant urban atmosphere.