The Lobstah Crawl: Seven Months, One Little Plane, and the Long Road to Oshkosh

Last updated October 28, 2026.

Picture this: a spring morning somewhere on the Carolina coast. We’re hitching up the fifth wheel for the next leg, and somewhere overhead, a little 1968 Piper Cherokee is climbing out over the marsh with our daughter at the controls, headed for the same town we are.

That’s the Lobstah Crawl. And I still get goosebumps thinking about it.

Trip at a Glance

• Dates: January – August 2027 (about seven months)
• Route: Florida up the East Coast to Maine, west to Oshkosh, Wisconsin, then home to Florida
• Planned stops: 20-plus in 13 states
• The finale: EAA AirVenture Oshkosh, July 26 – August 1, 2027
• Our rig: 2024 Jayco Eagle HT 29DDB fifth wheel, towed by our 2025 Ford F-350 6.7L diesel
• The plane: a 1968 Piper Cherokee 180, flown by Mack
• How we travel: 2–4 weeks at most stops, moving on weekends

The Planned Route

Our route is a plan, not a promise. For our family’s privacy, we share the campgrounds and airports we used after we’ve moved on from each stop, along with real dates and costs.

Jump to: Mack and her plane · Florida to the Carolinas · Mid-Atlantic · New England and Maine · West to Oshkosh · Home to Florida · FAQ

How This Started

We were still at AirVenture this past summer when we started talking about coming back. Mack had earned her pilot’s license just months before, and that week in Oshkosh felt like the moment her flying life really began.

Getting to Oshkosh this year was already an adventure in itself, with stops in Washington, D.C., Virginia, West Virginia, and Kentucky, plus a trip most of the way around Lake Michigan. So the question became: how do we top that next year?

That little question turned into a seven-month plan. We’ll set out from Florida in January, chase spring all the way up the East Coast to Maine, and then turn west for Oshkosh in July. Lobster rolls are non-negotiable, hence the name.

The Real Headliner: Mackenzie and Her Vintage Plane

Here’s the part that makes my heart beat a little faster. Mackenzie is now 18, she’s a private pilot, and she’s going to fly the entire East Coast.

While we drive the fifth wheel from stop to stop, Mack will be flying her almost-60-year-old Piper Cherokee 180, right alongside us. She’ll go from Tampa all the way up to Maine, and then west to Oshkosh. That’s well over 2,000 miles of coastline, mountains, and lakes, one hop at a time.

Every leg is a chance for her to build hours and experience: new airports, busy coastal airspace, changing spring weather, and real-world flying you just can’t get by circling your home airport over and over. She’ll plan each flight, check the weather, and make the go/no-go calls herself. And while we’re crawling along I-95, she’ll be looking down on lighthouses, barrier islands and harbors full of boats. (I’m only a little jealous.)

It has shaped the whole route, too. Every stop needs a good campground for the RV and a friendly little airport nearby for the plane. A few places came off our list simply because they’re a hassle to fly a small plane into (here’s to you, Washington, D.C.), and a few others made it on because of the flying. Landing at the Wright Brothers National Memorial? That one was never up for debate.

As parents, we’ll admit it’s a whole mix of feelings. Pride, mostly. A few nerves, definitely. It doesn’t feel like it was that long ago that she was the one in the back seat on our road trips. Now she’ll often be the one who gets there first. This will likely be our last big trip together before she heads off to college, and I can’t imagine a better way to spend it.

We’ll be sharing her flights here on the blog, too, so you can come along for the view from the left seat. And when she finally lands at Oshkosh at the end of all this? I already know we’re going to be a bit emotional.

Leg One: Florida to the Carolinas

The idea is simple: stay just ahead of the tourists and just behind the cold, and let the spring carry us north.

Tampa Bay and Central Florida

Planned: January · Can’t miss: a Space Coast rocket launch

Every good road trip needs a slow start, and ours begins in Tampa with some warm winter days to settle into our travel routine before the miles start adding up. Then we’ll swing inland to Kissimmee, our jumping-off point for a day at Kennedy Space Center (about an hour away) and, if the timing works out, the thrill of watching a rocket launch from the Space Coast.

St. Augustine, Florida

Planned: February · Can’t miss: Castillo de San Marcos

Founded in 1565, St. Augustine is the oldest continuously inhabited European-founded city in the continental U.S., and we’re not rushing it. We’re looking forward to wandering the brick streets of the old town, exploring the Castillo de San Marcos, climbing the lighthouse and taking in the beaches nearby. It’s the kind of place that rewards slowing down.

Georgia’s Golden Isles

Planned: February · Can’t miss: Driftwood Beach

Next up are St. Simons and Jekyll Island, a stretch of Georgia coast we’ve heard so much about. I can’t wait to photograph the bleached, twisted trees on Driftwood Beach and take long walks under the live oaks. We’ll also visit the historic Jekyll Island Club, once a winter retreat for families like the Rockefellers and Pulitzers.

The Lowcountry, South Carolina

Planned: March · Can’t miss: Charleston in bloom

If there’s a place made for spring, it’s coastal South Carolina. We’ll start in Bluffton and Hilton Head, with oysters from the May River and long walks along the beach. Then it’s on to Charleston, hopefully while the azaleas and gardens are in bloom. We’re picturing pastel houses, cobblestone streets, a boat ride out to Fort Sumter, and more shrimp and grits than is probably reasonable.

The Cape Fear Coast, North Carolina

Planned: April · Can’t miss: Battleship North Carolina

Wilmington and the beaches of the Cape Fear region will be our home for a while. We’re planning to walk the historic riverfront, tour the Battleship North Carolina, and spend lazy afternoons at the beach before the summer crowds arrive.

The Outer Banks, North Carolina

Planned: April · Can’t miss: the Wright Brothers National Memorial

For a family with a newish pilot, this one is a must. Kill Devil Hills is where the Wright brothers made the first powered flight in 1903, and there’s a small airstrip right at the Wright Brothers National Memorial where pilots can land and walk to the monument. Mack flying her Cherokee into the birthplace of flight? I can’t think of anything better. We’ll also climb a lighthouse or two and look for the wild horses up near Corolla.

Leg Two: The Mid-Atlantic and Hudson Valley

Virginia’s Tidewater

Planned: April · Can’t miss: Colonial Williamsburg

Basing ourselves in Williamsburg, in the heart of the Historic Triangle, gives us time for all three: Colonial Williamsburg, Jamestown and Yorktown. This is where so much of America’s story began, and we’re excited to soak up the history, the costumed interpreters and some very good taverns.

Cape May, New Jersey

Planned: April · Can’t miss: spring bird migration

Cape May sits at the very tip of New Jersey, with Victorian gingerbread houses, a classic lighthouse and wide, quiet beaches. It’s also a famous spot for spring bird migration, so I fully expect to come home with way too many bird photos.

The Hudson Valley, New York

Planned: May · Can’t miss: Old Rhinebeck Aerodrome

Rhinebeck and Hyde Park have both history and a big aviation bonus. In Hyde Park, we’ll tour FDR’s home and presidential library and maybe treat ourselves to a meal at the Culinary Institute of America. In Rhinebeck, the Old Rhinebeck Aerodrome is home to a collection of early aircraft from the pioneer and World War I eras. 

Leg Three: New England and Maine

Coastal New England

Planned: May – June · Can’t miss: Mystic Seaport

This is where the trip turns into a true seaside adventure. We’ll start in Mystic, Connecticut, exploring the historic ships at Mystic Seaport (and yes, a slice at Mystic Pizza). Then we’re on to Cape Cod, with its dunes, lighthouses, and national seashore. After that, we’ll split our time between Salem, Massachusetts, and Portsmouth, New Hampshire, both full of maritime history, old harbor towns and maybe a witchy story or two.

Midcoast and Downeast Maine

Planned: June · Can’t miss: sunrise on Cadillac Mountain

This is the heart of the Lobstah Crawl, and the stretch I’ve been dreaming about since we started planning. In Camden, we’ll watch the windjammers sail in and out of the harbor, hike up Mount Battie for the view, and visit the vintage planes at the Owls Head Transportation Museum. Then we head to Bar Harbor and Acadia National Park for a sunrise on Cadillac Mountain, the carriage roads and that famous rocky coastline.

The White Mountains, New Hampshire

Planned: July · Can’t miss: the Kancamagus Highway

From the coast, we’ll head inland to Lincoln, New Hampshire, for some fresh mountain air. We’re planning to drive the Kancamagus Highway, walk through Flume Gorge, and enjoy a little cool weather before the summer heat of the Midwest.

Leg Four: West to Oshkosh

The Finger Lakes, Niagara and Ohio

Planned: July · Can’t miss: Niagara Falls

The home stretch toward Oshkosh. We’ll stop in Canandaigua in New York’s Finger Lakes for lake views and wine country. Then comes a quick overnight at Niagara Falls, because how could we drive right past it? We’ll end in Archbold, Ohio, home to Sauder Village, a living history museum, and a good spot to catch our breath before the big finale.

Oshkosh, Wisconsin

Planned: July · Can’t miss: EAA AirVenture, July 26 – August 1, 2027

The finish line. A year after our first AirVenture, we’ll be back for the World’s Greatest Aviation Celebration, and if all goes to plan, this time Mack flies in. Seven months of flying up the coast, all leading to this one week. I’m already getting emotional just typing that.

Leg Five: Home to Florida

After AirVenture, we’ll quickly round out our trip, finishing in Florida, wherever Mackenzie will be starting college in the fall. The route will change along the way. It always does, and honestly, that’s half the fun.

Real Life on the Road

We’ll be doing all of this while living and working full time from the RV. We both still have full workweeks, plus Stefan’s regular business trips, so we’ll stay at most stops for one to two weeks and move on weekends instead of racing from place to place. After rushing through some of our favorite places out West, we want slower travel that lets us find the good local stops and really get to know a place.

Lobstah Crawl FAQ

How does a plane travel alongside an RV?

Mack flies on her own schedule for each leg while we drive the fifth wheel. We pick stops with a small airport nearby, so the plane and the RV end up in the same area. We’ll pick her up from the airport and be able to take sightseeing tours at each location, giving us a totally new perspective at each place. 

How do you choose campgrounds near airports?

Lots of research. There is a surprising number of executive and regional airports across America, which plays in our favor. We look for big-rig-friendly parks that are generally well-rated and, if possible, don’t have many full-time residents. Level pads are preferred but not a given!

How long will you stay at each stop?

This tour, our visits will usually last one to two weeks. We work Monday through Friday, so we move on weekends and use the extra time in to really explore.

How do you work full time from the road?

Working on the road is incredibly easy as long as we have Internet and phone connections. Starlink was a game-changer (read more in our Starlink review), and we all love working from our Apple MacBooks for their great reliability and long battery life. 

Where should we eat lobster?

We’re taking suggestions! Tell us in the comments.

Final Thoughts

When we decided to go full-time, this is exactly the kind of trip we were dreaming about. Seven months and one fifth wheel. A little airplane was never part of the original plan, and now we can’t imagine the trip without it. We’ll share the whole journey here: the campgrounds, the small towns, the flights, the food, and what it really looks like to live and work from the road for seven months. Join us in January as we take the Lobstah Crawl all the way to Oshkosh.

Have you traveled the East Coast? Tell us the lobster shack, harbor town or little airport we absolutely can’t miss!

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Campground, tourism board or airport along our route? We’d love to hear from you. Work with us.

Keep reading: Our Gulf Coast RV road trip: our first winter as full-timers · Our Jayco Eagle HT 29DDB review, two years later

More trips: see every road trip we’ve taken on our Where We Went page.