If you’re planning your first trip to Door County, you’re probably feeling a little overwhelmed—and that’s totally normal.

Because here’s the thing: Door County isn’t a single destination. It’s a whole peninsula of charming towns, state parks, scenic drives, hidden beaches, cherry orchards, and family-run restaurants. It stretches over 70 miles and offers more than 300 miles of shoreline, each bend in the road revealing something new.

And you might feel like you need to “see it all,” but I promise: you don’t. What you need is a thoughtful plan that focuses on a few iconic experiences—the kind that let you settle in, slow down, and truly feel the magic of this place.

A great Door County trip isn’t about cramming your schedule—it’s about anchoring your days around what makes this place special: cherries and sunsets, cozy cabins and winding roads, early-morning lakes and late-night laughter.

This post is your starting point. A way to dip your toe in without diving headfirst into every recommendation Google throws your way. I’ll share the moments that matter most—the “anchors” as I call them that I always tell my friends and family to build their trip around.

Whether you’re coming for one weekend or the start of a new tradition, this is how to do Door County right.

Get to Know Door County: Bay Side vs. Lake Side

The Bay Side—along Green Bay—is where you’ll find bustling harbor towns, patio dining, live music, and golden-hour sunsets you’ll never forget. Fish Creek, Ephraim, and Sister Bay all sparkle with energy and charm.

The Quiet Side—bordering Lake Michigan—is for early risers, nature lovers, and anyone craving stillness. Think rocky beaches, sunrises over the water, scenic hikes, and moments that feel completely untouched.

Rather than trying to stay somewhere new each night, I always recommend picking one place you love as a home base and planning each day in clusters. That way, you’re exploring intentionally—not backtracking or rushing from one end to the other.

Door County isn’t just a place to visit. It’s a place to feel. Early mornings on the lake. Farm stands on back roads. Nights around a fire. A slower rhythm you didn’t know you needed.

Maximize Your Drive In and Out of Door County

Your first trip to Door County should feel relaxing from the moment you cross the bridge—and that includes the drive. Instead of rushing in and out, make the most of your travel days by turning them into part of your vacation experience.

The Door County Coastal Byway is a 66-mile loop that wraps around the peninsula—up one coast, down the other—offering endless views of water, bluffs, barns, forests, and charm in every direction. Start just north of Sturgeon Bay, cruise up Highway 42 on the bay side, and plan your return on Highway 57 along the quieter Lake Michigan shore. It only takes about 60 minutes to drive from the bridge to the tip of the peninsula, but with the right stops, it becomes part of the magic.

Suggested Stops on Your Way In (Highway 42):

• Anderson Dock – Cool historic dock, great for pics.
• Peninsula State Park – Perfect for a quick scenic hike.
• Jens Jensen’s Winding Road – The very tip of the peninsula!
• Hatch Distilling Co. – Great cocktails and small batch spirits.
• Sister Golden – A must-stop if you love artsy, curated finds.
• Zeke’s Village Market – Best place to stop for some DoCo gear.

Suggested Stops on Your Way Out (Hwy 57):

• Cave Point – One of the most famous spots in DC!
• Door County Brewing – Grab a local brew, live music, food trucks and board games.
• Stone’s Throw Winery – Our favorite winery, grab some to bring home!
• Whitefish Dunes State Park – Another great hiking option.
• Cana Island Lighthouse – lighthouses are iconic in Door County and this is the coolest one.
• The Farm – visit baby farm animals? Doesn’t matter your age: yes, please.

📍Want even more options? Our interactive travel guide includes over 100 curated stops with photos, insider notes, and categorized filters so you can pick the ones that fit your vibe. Grab the guide here and turn your drive into a Door County highlight.

Where to Stay for Your First Trip to Door County

Now that you have the lay of the land and have started to plan your drive in and out of the peninsula, let’s talk about where to stay. It’s a highly debated topic, but in my opinion, going to Door County means going to the cabin.

It’s a place that invites you to slow down and experience life differently—surrounded by charm, on the water, and far from your usual fast-paced routine. There’s so much to explore across the peninsula, from north to south. My recommendation? Choose a home base that’s a destination in itself, then build mini itineraries based on some “anchor” spots as you venture out to explore the peninsula.

Whether it’s watching sunsets over the water, roasting s’mores by the fire, sipping morning coffee on the dock, or enjoying a cozy game night, Door County and cabins go hand in hand.

Top 4 Cabins to Stay in for Your First Trip to Door County

• The Bay on Clark Lake – A family-friendly, dog-welcoming retreat with floor-to-ceiling windows, kayaks and canoes included, and easy access to Cave Point and Whitefish Dunes.
• Porte Haven – Perched on a bluff above Death’s Door, this cabin was built on an old boathouse and features round porthole-style windows and views of four islands from the balcony.
• The Point – A spacious lakefront property on a private peninsula that sleeps up to 12, ideal for multi-generational trips or friend groups looking to reconnect by the water.
• Rowley’s A-frame – A peaceful A-frame surrounded by trees, complete with cozy corners, an outdoor firepit, and access to a private pier for morning paddles and quiet reflection on Rowley’s Bay.

Build Your Door County Itinerary Around These Anchors

Now onto the fun part! My best advice for planning your first trip to Door County? Don’t try to do everything. Pick a handful of truly unforgettable experiences—the kinds that capture the essence of this place—and build simple, thoughtful days around them.

Below, I’ve gathered my most recommended and favorite ideas, each centered around something iconic Door County is known for: sunsets, cozy cabins, all things cherry, time on the water, and more. These are the anchors I always suggest to friends and guests when they ask, “What should we make sure not to miss?”

Anchor: Take a Scenic Drive Through Door County

At the very tip of the peninsula, a quiet stretch of road winds through the trees in perfect S-curves. This is Jens Jensen’s Winding Road—designed by a Danish landscape architect who believed roads should make you feel something.

As you drive, notice how the light shifts through the canopy. How the trees arch just so. How the moment makes you breathe deeper. This road is iconic in every season, but fall? It’s a golden tunnel.

Sample Itinerary: On your way, stop by Hill House for dreamy home goods, then end your day with a slow dinner at Shoreline, where the sun dips into the lake as you toast to finding places like this.

Anchor: Explore the Charm of Ephraim at Sunset

Ephraim is the kind of place that makes you want to roll your windows down and linger. The bay sparkles, sailboats drift in the harbor, and whitewashed buildings glow in the fading light. Driving through at sunset feels like stepping into a simpler time.

Sample Itinerary: Grab a slice at Bad Moravian, then stroll to Anderson Dock where you can add your name to the graffiti-covered boathouse. If the moment calls for something sweet (and it always does), head to Wilson’s for ice cream before sipping wine at Pearl Wine Cottage as the sky turns to watercolor.

Anchor: Get on the Water at Cave Point

Cave Point is wild in the best way. Waves crash into limestone cliffs, carving caves you can explore by kayak. On the right day, if you’re brave enough, you can leap from the rocks into the icy blue water below. It’s a rush—and a core memory.

Prefer to stay dry? Just watching the water swirl into the caves is a show in itself.

Sample Itinerary: Before or after, stop to feed baby goats at The Farm, browse the art at Woodwalk Gallery, and wrap it up with wine tasting at Stone’s Throw before a supper club dinner at Donny’s Glidden Lodge.

Anchor: Climb Cana Island Lighthouse

The path to Cana Island Lighthouse starts with a causeway. Sometimes you walk. Sometimes a tractor pulls you through the water. Either way, it feels like the beginning of an adventure.

Climb 97 steps to the top and take in sweeping views of Lake Michigan. It’s windy. It’s wild. It’s worth it.

Sample Itinerary: Start your morning with a breakfast burrito from Good Eggs, stop by Door County Alpaca Ranch to meet the fluffiest locals, and let this lighthouse climb be the high point of your day—literally and figuratively.

Anchor: Dine at a Farm-to-Table Favorite

Door County’s food scene is quietly extraordinary. One of my favorites? Chives in Baileys Harbor. With seasonal menus, locally grown ingredients, and an ambiance that strikes the perfect balance between elevated and welcoming, it’s a must.

Sample Itinerary: Spend your afternoon hiking The Ridges Sanctuary, browsing the interior design finds at Nathan Nichols, or enjoying a pre-dinner beer at Door County Brewing Co. before settling into an unforgettable meal.

Anchor: Stay in a Door County Cabin

You could stay in a hotel, sure. But cabins and Door County go hand in hand. Waking up to lake views. Brewing coffee barefoot. Roasting s’mores under a blanket of stars. Game night around the table with no rush to go anywhere.

When you stay at one of our cabins, you’re not just booking a bed—you’re creating space for slow mornings, spontaneous moments, and memories that outlast any souvenir.

Sample Itinerary: Rent a mobile sauna, have a private chef visit the cabin from Door County Underground

Anchor: Catch an Iconic Door County Sunset

Some sunsets in Door County stop you in your tracks.

Door Bluff Headlands County Park is one of those places. A short hike through the woods leads to a quiet cliffside overlook. No crowds. No noise. Just trees, sky, and the water far below turning to gold.

If you want the classic sunset-in-the-village feel, head to Sunset Beach Park in Fish Creek. People gather each evening with blankets, wine, and ice cream cones to watch the day fade. It’s simple and timeless.

Anchor: Taste the Flavors of Door County Cherries

Door County is the Cherry Capital of the Midwest. The climate here produces millions of pounds of tart cherries each year, and whether you come in spring to see the blossoms or summer to pick your own, it’s part of the experience.

Don’t leave without:

• Trying the cherry mule at Chop
• Buying cherry salsa from Lautenbach’s Orchard
• Ordering the cherry French toast at White Gull Inn

(And yes, we always grab a bottle of cherry vodka to take home from Welsing’s Foodland before heading out of town.)

One Last Thought Before You Go

I’ve helped thousands of first-time guests plan their trips to Door County through our cabins—and you know what happens? They come back. They fall in love. They bring more people next time.

So if this is your first time visiting, don’t stress. Just start with the experiences that speak to you. Leave room for slow mornings and sunset detours. Use these anchors as your guide, then layer in your own discoveries. You can always come back—and my guess is, you will.

Ready to Make It Happen?

Want the full experience laid out for you?

Grab our Door County Travel Guide, complete with curated itineraries, restaurant picks, hidden gems, and an interactive map that helps you plan the kind of trip people will be asking you about for years.

Because years from now, it won’t be the to-do lists or the planning stress you remember. It’ll be the moment you stood by the lake and thought: “This is exactly where I’m meant to be.”