One of his biggest goals? Hiking a portion of the Appalachian Trail (AT) as a way to disconnect, reflect, and prepare for his next chapter after service. But a trip like this doesn’t just happen—it takes thoughtful financial and logistical planning. Here’s how we made it work:

Two Years of Intentional Planning

When we moved to Kentucky from Hawaii two years ago, we knew this would be our final duty station. That’s when my husband began outlining his retirement timeline, carefully saving his leave, and considering how he wanted to transition into post-military life.

As the AT hike became a serious goal, we began discussing the financial aspects. His sisters had hiked a portion of the trail a few years ago and shared valuable insights. From there, we created a checklist of essential gear, food supplies, and tracking equipment. Instead of making large, last-minute purchases, we spread out our expenses over two years, buying items gradually to avoid financial strain.

The Cost of Hiking the Appalachian Trail

According to Google, the average cost for an Appalachian Trail thru-hike ranges from $5,000 to $7,000, including gear, resupply packages, and town expenses. The estimated monthly cost is around $1,000 for food, lodging, and other essentials.

For our trip, we carefully budgeted and planned ahead:

• Gear & Resupply Packages: We spent approximately $4,000 on gear and pre-planned resupply shipments to help manage costs and ensure my husband has the essentials on the trail.
• Town Expenses: We estimate spending around $1,000 on hostel stays, laundry, meals, and transportation (shuttles/Ubers) when my husband stops in towns along the way.

By spreading out these costs over two years, we avoided large financial burdens and ensured my husband could fully enjoy this experience without financial stress.

Aligning the Hike with Retirement Logistics

Once he received his retirement orders, we mapped out key dates—his Change of Responsibility ceremony, VA appointments, potential Career Skills Program (CSP) opportunities, and his official retirement ceremony. All of these factors impacted when he could embark on the trail. Initially, he hoped to hike for 60 days, but after reviewing his commitments, he adjusted his plan to a 35-day trek.

Involving Our Son in the Journey

As we fine-tuned our plans, we realized this experience could be even more meaningful. Our 17-year-old son decided to join his dad for 50 miles of the hike during spring break. We factored this into our financial and travel planning, ensuring I could pick him up at a designated spot while my husband continued his journey.

More Than a Hike—A Financial and Life Transition

For us, this Appalachian Trail journey isn’t just about the hike—it represents a carefully planned transition into retirement. By budgeting for this adventure in advance, aligning it with our financial goals, and ensuring my husband has the time and resources to pursue his dream, we’ve set the stage for an exciting new chapter.

At MainStreet Financial Planning, we believe financial planning isn’t just about numbers—it’s about making dreams achievable. Whether it’s planning for retirement, a big life goal, or a career transition, having a solid financial strategy makes all the difference.

Are you preparing for your next big life adventure? Let’s plan it together.

The post Financial Planning for Life’s Big Adventures: How We Prepared for My Husband’s Appalachian Trail Hike appeared first on MainStreet Financial Planning.

After my mom passed, I had been helping my dad get his estate planning documents and other financial activities in order. In fact, when on the phone with his insurance or investment companies, he loved to refer to me as his financial advisor before even mentioning that I was also his daughter. Over the years my dad felt comfortable that everything was in in good hands for when he passed.

Below are some of the items or activities my dad and I did.

• Add data to an Excel spreadsheet.

• • Use a Life Organizer to collect your important data as shown in this Money Tip. I made sure it included a list of my dad’s former addresses, email addresses and phone numbers, personal information like date of birth and Social Security number and military data. After he passed, it was great to be able to not only have everything in one place but where I could copy and paste data instead of constantly retyping.

• Create an address book with the people you want to attend your funeral, including phone numbers.

• • I had a few weeks before my dad’s military funeral was scheduled so I was able to mail letters, however, most of the time the funeral will be coming up pretty quickly and letters are not an option. My dad’s friends greatly appreciated being notified.

• Write your own obituary

• • What is it you want your family and friends to know about you and what you value most? Not only is this task out of the way for those you leave behind but it’s also a good recap of your life so far!

• Make a list of your values or create a letter of intent.

• • This lets your family know what’s important to you or if you have instructions on what you wish your heirs to do with the funds you’ve left them.

• Have a family meeting

• • This is where you can discuss what the documents are, what your family’s responsibilities are, and get on the same page with your wishes if you become incapacitated or pass away. Not everyone is ready to face this topic head-on—be prepared for jokes brushing it off, procrastination or denial.

• Do a test run

• • The worst time to realize your hard work wasn’t actually complete is after you’ve passed and there’s nothing that can be done. So, practice! Have your executor do a test run trying to locate your documents and check they have any needed contact information while you’re still around to fill in the gaps.

My client’s father had his documents in “the red notebook” which I thought was pretty genius. Not only did this notebook contain his letter of intent—instructions for some funds earmarked for the grandchildren towards purchasing a car, but the name “red notebook” will now always refer to a source of all the important information a family needs when someone passes away. Instilled in the next generation, it becomes a legacy passed along to the rest of the family who will also make sure they are as prepared as they can be.

For another article on getting ready for your end of life, see this article on Digital Legacy Planning to organize your online assets.

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