Shorewood

Day Trips

Make the most of your day with our curated plans, packed with Shorewood's hidden gems and unique experiences!

day 1
Exploring Historic Center
morning
:

Start your day with a hearty breakfast at a local café in Shorewood, enjoying freshly brewed coffee and homemade pastries. After breakfast, take a leisurely stroll through the charming streets of the historic district, admiring the unique architecture and vibrant local shops. Stop by the Shorewood Historical Society to learn about the town's rich history and significant landmarks.

afternoon
:

In the afternoon, explore the local art scene by visiting the Shorewood Art Gallery, showcasing works from regional artists. Enjoy a light lunch at a nearby sandwich shop, where you can savor farm-to-table ingredients. Afterward, participate in a guided walking tour that highlights the history and culture of Shorewood.

evening
:

As evening approaches, unwind at a cozy bistro that offers a selection of local wines and craft beers. Enjoy a delicious dinner featuring seasonal produce and regional specialties, while listening to live music. To wrap up your day, take a sunset stroll along the scenic shoreline, soaking in the tranquil views of Lake Michigan.

day 2
Beach and Water Sports
morning
:

Kick off your beach day with an energizing breakfast at a beachfront café, where you can enjoy ocean views with your meal. Afterward, head to the local beach to soak up the sun and enjoy the refreshing waters of Lake Michigan. Rent a kayak or paddleboard to explore the shoreline and get a unique perspective of the surrounding area.

afternoon
:

Spend your afternoon engaging in various water sports, such as jet skiing or windsurfing, with equipment available for rent nearby. After working up an appetite, enjoy a picnic lunch on the sand, complete with local snacks and refreshments. Don’t forget to take breaks to relax and enjoy the sun, or participate in beach volleyball games with other visitors.

evening
:

As the sun sets, gather around a beach bonfire for a classic evening experience, roasting marshmallows and sharing stories. Head to a nearby seafood restaurant for a dinner featuring fresh catches of the day and local favorites. Cap off your evening with a moonlit walk along the shore, enjoying the sound of waves lapping against the sand.

day 3
Nature Walks and Wildlife Viewing
morning
:

Start your day with a healthy breakfast at a local diner, fueling up for a day of adventure in nature. After breakfast, head to the nearby nature reserve, where you can immerse yourself in the beauty of Shorewood's native flora and fauna. Enjoy a guided nature walk that introduces you to the local ecosystem and its inhabitants.

afternoon
:

In the afternoon, explore the trails at your own pace, taking time to spot various bird species and other wildlife along the way. Bring a packed lunch to enjoy at a scenic viewpoint, surrounded by the peaceful sounds of nature. Consider visiting the nearby botanical garden to learn about the diverse plant life native to the area.

evening
:

As the day winds down, head back to your accommodation to freshen up before dinner. Enjoy an outdoor dining experience at a restaurant that specializes in farm-to-table cuisine, offering seasonal dishes made from locally sourced ingredients. Conclude your day with a stargazing session at the nature reserve, where the lack of city lights allows for a breathtaking view of the night sky.

day 4
Culinary Exploration
morning
:

Begin your day with coffee and pastries at a popular local bakery, known for its artisanal offerings. Attend a cooking class where a local chef teaches you how to prepare traditional dishes, incorporating fresh, local ingredients. This interactive experience sets the stage for a day filled with culinary delights.

afternoon
:

After mastering some new dishes, enjoy a leisurely lunch at a farm-to-table restaurant that highlights Shorewood's local produce. Explore the local farmers market where you can sample fresh fruits, vegetables, and homemade products, and chat with the vendors. This afternoon of tasting and shopping provides insight into the local food culture.

evening
:

In the evening, embark on a guided food tour that takes you to several of Shorewood's best eateries, trying a variety of dishes from different cuisines. Pair your meals with local wines or craft beers, enhancing the flavors of each dish. End your culinary adventure with dessert at a charming café, known for its decadent treats.

day 5
Art and Culture Immersion
morning
:

Start your day with a visit to a local art studio, where you can take part in a painting workshop led by a Shorewood artist. Enjoy breakfast at the studio's café, surrounded by inspiring artwork and creative energy. This hands-on experience allows you to express your artistic side while learning about local art techniques.

afternoon
:

In the afternoon, visit the Shorewood Cultural Center, where you can explore various art exhibitions and cultural displays. Attend a lecture or workshop about local history or art, gaining deeper insights into the community's cultural heritage. Take a break for lunch at a nearby café, where art and cuisine blend seamlessly.

evening
:

As evening falls, enjoy a theatrical performance at a local community theater, showcasing the talents of regional actors and directors. After the show, attend a meet-and-greet with the cast to discuss their creative process and inspirations. Finish your day with dinner at a restaurant that features artwork from local artists, creating a vibrant atmosphere.

day 6
Local Festivals and Events
morning
:

If your visit coincides with a local festival, start your day by attending the opening ceremonies, filled with music and local traditions. Grab breakfast from food stalls offering regional specialties and enjoy the festive atmosphere. Explore the various booths showcasing local artisans, crafts, and community organizations.

afternoon
:

Continue your celebration in the afternoon by participating in various activities, such as cooking demonstrations, craft workshops, or live entertainment. Sample dishes from local food vendors and enjoy live music performances, immersing yourself in the local culture. Take time to interact with residents and learn about their traditions and community pride.

evening
:

As the day transitions into evening, enjoy the festival's evening entertainment, which may include dancing, concerts, or fireworks. Join the locals in celebrating the community spirit with food and fun. Conclude your night with a sweet treat from a festival vendor, cherishing the memories of the day's festivities.

day 7
Shopping and Relaxation
morning
:

Begin your day with brunch at a charming café known for its breakfast specials and relaxed atmosphere. Afterward, stroll through Shorewood’s boutique shops, where you can find unique clothing items, handmade crafts, and local souvenirs. Take your time exploring each shop and interacting with friendly shop owners.

afternoon
:

Spend your afternoon at a local spa indulging in a rejuvenating massage or facial treatment, allowing yourself to unwind. After your spa experience, grab a light lunch at a nearby café that focuses on healthy, organic options. Enjoy the rest of your afternoon with a leisurely walk in the local park, soaking in the serene surroundings.

evening
:

As evening approaches, enjoy dinner at a cozy restaurant that offers a menu filled with comfort foods and seasonal dishes. After dinner, consider visiting a local wine bar to sample wines from nearby vineyards and relax in an inviting atmosphere. End your day with a nightcap, sharing stories and laughter with friends or loved ones.

day 8
Adventure and Outdoor Activities
morning
:

Start your day with an adrenaline rush by having breakfast at a local diner, then heading out for a day of adventure. Join a guided cycling tour that takes you through Shorewood’s scenic routes, showcasing beautiful landscapes and iconic landmarks. Enjoy the fresh air and invigorating exercise as you explore the area on two wheels.

afternoon
:

In the afternoon, take a break for lunch at a park, enjoying a packed meal while surrounded by nature. Afterward, continue your exploration with activities such as rock climbing or zip-lining at a nearby adventure park. This thrilling experience will give you a new perspective of the great outdoors.

evening
:

As the sun sets, return to Shorewood for a well-deserved dinner at a restaurant known for its hearty fare. Share your adventure stories with fellow diners, discussing the highlights of your day. Conclude your evening with a relaxing walk through the town, enjoying the vibrant nightlife and local ambiance.

Discover Shorewood

Read more in our Shorewood 2025 Travel Guide.

Shorewood Travel Guide