Skylar is a Texas-based wedding planner & designer sharing her sanity-saving processes & templates.


Discovering Door County: Unveiling Our Annual Family Tradition

Welcome to Door County, a place where time seems to slow down, and the essence of family togetherness comes alive. In this charming corner of the world, we gather each year with our extended family of 29, joined by two other wonderful families, for an annual retreat that has become a time-honored tradition. As the July sun paints the horizon with its golden hues, we enjoy a week filled with love, laughter, and cherished memories that will last a lifetime. Join me as I share the magic of Door County, a hidden gem tucked away in the picturesque landscape of Wisconsin, where quaint towns, stunning vistas, and cherished traditions intertwine to create an unforgettable summer vacation.

The Hallmark-Worthy Story Behind The Annual “Bay Shore” Trip

Picture this: a story so captivating, it could be straight out of a Hallmark movie. Now, how much fiction has found its way into the retelling of this tale within our family remains a delightful mystery. The narrative, as I’ve always heard it, begins with my mother-in-law’s parents embarking on a journey with their three spirited daughters, bound for a water skiing adventure on the Great Lakes. However, fate had other plans.

When their car developed an unexpected issue, they found themselves seeking refuge in the charming town of Sturgeon Bay, Wisconsin, hoping for a quick repair. Little did they know that this serendipitous stop would forever change the course of our family’s history. With the car repairs requiring more time, they sought shelter at The Bay Shore Inn, a collection of a-frame cabins and a humble mess hall back then. As if by magic, the inn’s inviting pool became an instant playground for the girls, forging fast friendships. When it came time to hit the road again, the pleas from the girls to extend their stay were irresistible. And so, my mother-in-law’s parents caved to the girls and even befriended three other families who had also discovered the hidden gem of The Bay Shore Inn. The question echoed among the laughter and splashes, ‘Same time next year?’

View from South Building Balcony at The Bayshore Inn

And thus, over 50 years and four generations later, families both blood-related and honorary still gather at The Bay Shore Inn for a cherished week of relaxation and pure enjoyment. We raise glasses at mingling cocktail parties, tee off for memorial golf scrambles, and, if you’re anything like me, spend blissful hours lounging by the pool. It’s a tradition I wholeheartedly embraced long before Matt and I said, ‘I Do’.

After over eight years of returning to Door County with our family, I can wholeheartedly recommend it as an idyllic summer vacation spot. And let me tell you, I’ve gathered a treasure trove of tips to help you make the absolute most of your time there.

Getting to Door County

To reach Door County, many of the families, including most of ours, embark on a delightful road trip. But fear not if you prefer not to drive the entire distance, as there are semi-convenient options to fly into either Chicago (our go to, approximately a 4-hour drive away) or Green Bay (only a short 45-minute drive away, but prices are typically higher).

Now, when it comes to booking accommodations, I must admit that my expertise lies mainly within the realm of The Bay Shore Inn (BSI), our cherished home-away-from-home throughout the years. While I find its charm and waterfront views worth it, I understand that the smaller pool and more classic interiors may not suit everyone’s preferences. But fear not! Door County thrives on tourism, which means you’ll find an abundance of options, including hotels, home rentals, and even a couple of resorts, ensuring there’s something for everyone.

The Lodge at The Bayshore Inn, 2022 (100 Year Celebration)

However, before you dive into the wonderful world of accommodations, you’ll first need to choose which of the delightful small towns will serve as your perfect home base.

  • Sturgeon Bay: This vibrant town serves as the gateway to Door County, offering a bustling urban downtown, charming waterfront, and a rich maritime history. (This is where BSI is located)
  • Sister Bay: Known for its picturesque shoreline, Sister Bay beckons with sandy beaches, charming shops, waterfront dining, and its iconic waterfront park.
  • Egg Harbor: Nestled on the shores of Green Bay, Egg Harbor boasts stunning sunsets, quaint boutiques, delectable dining options, and a vibrant arts scene.
  • Fish Creek: A beloved destination for its stunning nature, Fish Creek offers breathtaking Peninsula State Park, charming shops, galleries, and the famous Fish Creek Beach.
  • Ephraim: Immerse yourself in Ephraim’s timeless beauty, characterized by its white-picket-fenced cottages, scenic harbor, historic landmarks, and serene atmosphere.
  • Bailey’s Harbor: Nature enthusiasts will find solace in Bailey’s Harbor, with its natural beauty, tranquil beaches, outdoor recreational opportunities, and the picturesque Ridges Sanctuary.

While we typically enjoy day trips to each of these charming towns (more on that later), selecting one as your home base will simplify your search for accommodations and help establish the perfect ambiance for your vacation.

Once you’ve settled into your cozy retreat, it’s time to dive into the plethora of activities and experiences that await in this captivating corner of Door County.

What to Do in Door County



There are seemingly endless small shops and boutiques to pop into all along the coastlines. Here are a few of my favorites:

  • Marketplace (Sturgeon Bay) — Lola May’s Boutique inside is always a must for me
  • Jackalope Trading Company (Baileys Harbor) — beautiful handmade goods with a side of “woo”
  • Blacksmith Clothing Co. (Egg Harbor) — women’s and men’s boutique
  • On Deck (Fish Creek, Sister Bay, Sturgeon Bay) — active and fashion clothes, usually with massive sales
  • Space & Spot (Sister Bay) — clothing & gift shop with humorous items


Skylar circa 2014 on her first every golf outing

While not exactly my regular cup of tea, if you love golfing in great weather, Door County has a variety of golf courses based on your crews’ skill level and budget. Our “splurge” every year is The Orchards in Egg Harbor. Other regular stops include Cherry Hills (very budget-friendly option) and Idlewild (affectionally known as “The Swamp” amongst our golfers).


Whether it’s a simple walk from the parking lot to the Cana Lighthouse for incredible views or going on a full-day hiking/kayaking/biking excursion to Washington Island, Door County is perfect for nature lovers to want to spend as much time in the incredible outdoors as possible.


If you’d asked me when I first started going on this trip for food recs, I’d tell you it was less about the food and more about the experience of Door County. But I’m happy to report that the influx of millennials thanks to low cost of living and relocations after the pandemic, there is a marked difference in what’s available for the foodies in Sturgeon Bay.

Here’s a list of some of our “Best Of”:


One of the most cherished aspects of our annual trip are the delightful traditions that have woven themselves into the fabric of our gathering. These quirky and fun moments have become time-honored highlights that we eagerly look forward to year after year. While I do believe that traditions are often best built organically, I must admit, I’m all for giving them a little nudge along the way ;). Allow me to share some of my personal favorite traditions that have become beloved staples of our time together:

Cocktail Parties

Our already bustling crew of 29, comprising of our extended family, makes for quite the lively gathering. However, when you add in the two other extended families who join us on this annual pilgrimage to BSI, it’s easy to see how the hubbub can make it challenging to connect with everyone. Now, I genuinely do not know the origins of the cocktail parties. But in their current form, they have become a cherished tradition. Each family takes a turn hosting a cocktail party during the week, where the hosts provide a simple selection of wine, beer, and light appetizers, often featuring classic Midwestern dips and veggie trays. We gather for about an hour before heading our separate ways for dinner, and it’s a wonderful time to catch up with one another and set the stage for some of our other cherished traditions.

The Cindy Strange Golf Scramble

Cindy, a cherished member of one of the other families who embarked on the original trip, holds a special place in our hearts, even though she passed before I joined the group. Her spirit lives on through one of her favorite traditions: The Golf Scramble. This tradition pays homage to Cindy’s memory and brings us all together in the spirit of fun and camaraderie. The scramble begins with a drawing during our family’s cocktail hour, where participants are split into partnerships. We strive for fairness by pairing ‘A’ golf players with ‘B’ golf players. The idea is to mix up families and partnerships, ensuring that we all have the opportunity to spend time with someone who isn’t our usual vacation buddy. It’s all about fostering connections and enjoying the experience together. The winners of the scramble are awarded a trophy and some Bay Shore Inn swag, typically in the form of cozy sweatshirts. And let’s not forget about the biggest ‘losers’—even they receive a prize, usually in the form of mugs or thermoses from BSI. Even as someone who only plays golf once a year during this scramble, it’s still a tradition that holds a special place in my heart. In fact, I’ve taken on the role of scramble coordinator, ensuring its smooth execution and carrying on Cindy’s legacy.

The Boot

Matt & ‘The Boot’, 2022

Ah, Das Boot, the annual tradition of indulging in a craft beer from a glass boot! This beloved ritual was born from the passion for beer of one of our attendees, whom we’ll affectionately call “A” for now. When it’s A’s family’s turn to host their cocktail party, we eagerly anticipate the grand appearance of the boot. It arrives filled to the brim with delightful brew, ready to be enjoyed by all. We gather in a spirited circle, each grasping the glass boot tightly. As tradition dictates, we begin by clicking the glass on the left, toasting ourselves for good luck. Then, with gusto, we down as much of the beer as we can before clicking the glass on the right, bestowing good luck upon the next person in line, and passing it to the right. There’s nothing like watching your husband’s 90-year-old grandmother drink from a boot full of beer. And, I must confess, during my first year, I even dared to surprise everyone by fearlessly finishing off the backwash in the toe of the boot. (Rest assured, for those with concerns, we introduced a modified version during the pandemic for those who prefer not to share a communal glass. They receive a little cup filled with beer exclusively for their enjoyment when it’s their turn.)

As another enchanting chapter in our time in Door County comes to a close, I can’t help but be filled with gratitude for the cherished memories we’ve created and the enduring traditions that bind us together. The allure of this delightful Wisconsin treasure lies not only in its scenic beauty and charming towns but also in the cherished moments spent with loved ones. From savoring craft beer from a glass boot to the joyous rounds of the Golf Scramble, each tradition carries with it a touch of whimsy and a dash of nostalgia. And as we bid farewell to Door County for now, we carry with us the promise of returning next year to continue this delightful journey of togetherness. So, to all who seek an idyllic summer escape, consider Door County your destination of choice—a place where laughter echoes through lush landscapes and the bonds of family grow stronger with each passing year. Until we meet again, I raise my glass to the beauty of tradition, the magic of togetherness, and the joys of summer vacations.

© 2018 showit template BY WITH GRACE AND GOLD.

Get email notices when new templates & freebies are added to the shop!

new content

Don't Miss out on

Photography by Smith House Weddings