7 Tips for a Fulfilling Retirement in Wisconsin
Jun 13, 2025
Retirement is not just a milestone; it’s a new chapter filled with opportunities to explore, connect, and embrace a lifestyle that reflects your values and aspirations. For many, retiring in Wisconsin offers a unique combination of natural beauty, supportive communities, and an enriching pace of life. At The Westerly Pewaukee, we understand how personal and significant this transition can be. That’s why we’re sharing seven thoughtful tips to help you create a fulfilling retirement right here in the heart of the Badger State.
1. Understanding Retirement Income and the Cost of Living in Wisconsin
When considering where and how to retire, understanding your financial picture is essential. Wisconsin offers a slightly higher overall cost of living than the national average, but it remains a practical option for retirees who want to stretch their retirement savings while maintaining a comfortable lifestyle.
That said, Wisconsin is a mixed bag when it comes to retirement income. Certain forms of income, such as Social Security, are exempt from state taxes, while others—like 401(k)s and IRAs—may be taxed. Understanding your regular income streams and working with a financial advisor can help you plan appropriately.
It’s also important to consider transportation and grocery costs in different regions. While certain cities may carry a higher price tag, places like Pewaukee offer a balance of affordability and quality amenities. At The Westerly Pewaukee, residents benefit from inclusive monthly pricing that supports both lifestyle and financial clarity, with many essentials—like housekeeping and utilities—already covered.
2. Choose the Right Community to Enhance Your Retirement Lifestyle
Choosing where you live in retirement is about more than square footage; it’s about the life you’ll build and the people you’ll share it with. Most retirees find the greatest satisfaction in communities that offer opportunities for both independence and support.
The Westerly Pewaukee was designed to meet these needs with heart. Nestled in Wisconsin’s Lake Country, our community supports residents in every stage—from vibrant independent living to compassionate memory care. Thoughtful amenities, beautiful common spaces, and engaging programs encourage real connection, making it easier to build friendships, stay active, and live with purpose.
This is especially important for retirees who are moving from areas where they may have been more isolated or far from loved ones. The right community, like The Westerly, provides not just a place to live—but a place to thrive.
3. Take Full Advantage of the Outdoors with Wisconsin’s Beautiful Lakes and State Parks
Retirement is your chance to reconnect with nature—and Wisconsin holds some of the Midwest’s most inspiring landscapes. With numerous state parks, beautiful lakes, and easy access to outdoor activities, this state is a favorite destination for outdoor enthusiasts.
Whether it’s walking scenic lakeside trails, kayaking in Lake Country, or enjoying birdwatching during a peaceful morning, spending time outdoors can boost both physical and emotional well-being. Lake Michigan, just a short drive away, offers a stunning backdrop for day trips and coastal exploration, while Pewaukee Lake provides everyday beauty right at your doorstep.
The Westerly Pewaukee’s location places you near some of Wisconsin’s most beloved outdoor spots, making it easier to stay active and inspired in every season.
4. Prioritize Elderly Healthcare and Access to Medical Care
Quality medical care becomes increasingly important as we age. Thankfully, Wisconsin recently coming into national focus for its strong health systems offers peace of mind. The state has a strong ranking for elderly healthcare, particularly in metropolitan areas like Milwaukee and Madison, with access to specialists and high-quality hospitals.
At The Westerly Pewaukee, health and wellness are integral to daily life. Residents have access to in-residence primary care services through a network of trusted providers. Whether you need regular wellness checks or more advanced support, compassionate care is available in the comfort of our community.
For most retirees, this level of access and continuity can make a meaningful difference—reducing the stress of scheduling, driving, and managing multiple providers.
5. Explore Local Culture and Enrichment for a Meaningful Retirement Lifestyle
Living in Wisconsin offers more than just affordability—it offers enrichment. Local events, community arts, seasonal festivals, and continuing education programs are plentiful throughout the state. Pewaukee and the surrounding Lake Country area boast a vibrant culture of music, food, and the arts that invites exploration year-round.
The Westerly supports this engagement through group outings, on-site clubs, and social opportunities that keep your days full and meaningful. Our Comet Club Social Bar, Rooftop Patio, and Spinnaker Club Room are just a few of the places where residents gather to celebrate milestones or simply enjoy each other’s company.
Often, what retirees completely overlook is how much joy can come from the simple pleasure of being part of something bigger than yourself.
6. Stay Flexible with Transportation and Everyday Needs
Mobility is a key component of independence in retirement. While some areas of Wisconsin can be car-dependent, certain cities like Pewaukee strike a balance between accessibility and tranquility. Public and private transportation options ensure you’re never far from the places and people you care about.
The Westerly Pewaukee offers scheduled group transportation for shopping and local events, helping residents enjoy freedom without the hassle of traffic or parking. For those who prefer to drive, we offer climate-controlled underground parking and proximity to local conveniences.
Managing errands, appointments, and social visits becomes significantly easier—and safer—when transportation is planned with intention.
7. Embrace the Emotional Journey of Retirement
Retirement is not just logistical; it’s emotional. The shift from a structured work life to open-ended days can bring both excitement and uncertainty. That’s why a supportive environment is key to feeling grounded during this transition.
Many retirees expect the financial part of retirement to be the hardest, but it’s often the emotional side—the change in routine, the need for new identity, the space for reflection—that requires the most attention. That’s also why choosing a community like The Westerly Pewaukee matters so much.
We offer a nurturing environment that honors each resident’s unique journey. From morning coffee chats in our Swan Tea Room to films in the Movie Theater or gentle exercise in our fitness center, everything is designed to support a meaningful and connected lifestyle.
You deserve a retirement that doesn’t just meet your needs but enriches your spirit.
Retire Confidently in the Heart of the Badger State
Retiring in Wisconsin means more than choosing a location—it means choosing a lifestyle filled with beauty, comfort, and connection. With its access to high-quality medical care and abundance of outdoor activities, Wisconsin stacks up well for those ready to enjoy the fruits of their retirement savings.
At The Westerly Pewaukee, we’re here to help you retire confidently. No matter what you’re looking for, our team is here to walk alongside you. Every day at The Westerly is another chance to embrace new experiences and live with intention.
Ready to take the next step? We invite you to get in touch with us today to learn more or to schedule a personal tour of our community. Let’s explore together what a fulfilling retirement in Pewaukee can look like for you or your loved one.