Midwest Travel Bucket List (2025 Version)
+ why being "cringe" is cool
This week was so, so many things.
It went by really fast, like I blinked and it was Friday. It was shockingly, jarringly cold and I kept forgetting until I walked outside. I write these newsletters on Friday evenings, and then schedule them for Sundays; right now, writing this, I honestly couldn’t tell you what I did this week. It all feels like kind of a blur.
I feel like I spent a lot of the time day dreaming about the rest of the year and things I have planned. Speaking of…
My 2025 Midwest Travel Bucket List (most ideal version)
Are you a travel bucket list kind of person? I love to sit down and make a list of all the places I plan to go, things I plan to do. Here’s my dream, most ideal, definitely won’t get to do all of this, 2025 travel bucket list:
Canyonlands and Arches National Park - this one is pretty much planned! Last early spring/late winter I did a backpacking trip out in the desert, and it was such a nice chance of pace and scenery that I’m planning another one this year. I might even make a little desert spring break thing an annual trip for me :)
Door County, Wisconsin - I’ve never been to Door County, and it’s one of the places I get asked about most often. I don’t have anything planned yet, but it’s softly on my radar to make a trip down here with my kayak this summer. (this one realistically won’t happen).
Keweenaw Peninsula in the Winter and Summer - Last winter I spent some time exploring the Keweenaw and I’m SO excited to be heading back in the very near future. I visited in the summer a long time ago, and I’d love to go back this year.
Some of the more hidden wilderness spots throughout the UP - There’s a small list of places throughout the Upper Peninsula of Michigan that I’d really like to try backpacking and camping! I’ll share more about those after I actually visit them.
Petoskey and Traverse City, Michigan - I’m hoping spend some more time this summer here, near my family. I spent a lot of time in this area in college and I know there’s both some places I’d like to get back to and others I’d like to visit for the first time.
Driftless Region - Last summer, I had the opportunity to explore the Driftless Region of Wisconsin on what had to be the hottest few days of the summer. I really, really liked it there and I would love to go back, but I doubt I’ll get the chance this year.
Those are the hard, checklist-style places I would like to go. Ideally I’d also like to get out for a solo paddle in the Apostles, and backpack the Pictured Rocks too. We’ll certainly see. There are also just three islands out of 21 that I have yet to make it to in the Apostles! I’d like to check out those places!
But beyond the measurable list of places, there are somethings I would like to do that aren’t necessarily so concrete:
Go solo car camping on a small road trip - last spring I did a big long car camping road trip through the Southern Midwest, and while that was super fun, I think this year is my year for really appreciating the adventures I can have near me. I think I’m going to do mini, weekend road trips within 3-4 hours of home instead of big, long haul adventures.
Try some of the backpacking routes near me - In the same vein of appreciating what’s around me, there are so many short and sweet backpacking routes in the Wisconsin Northwoods and Western Upper Peninsula, and I’m really excited to hopefully try out some of those quiet, less classically beautiful routes.
Have a beach fire at sunset - This is low hanging fruit for me, but even though I won’t be full-time guiding this summer, I still want to channel my inner kayak guide summer for sure! Part of that will be super possible in that I still have three custom women’s paddling trips running this summer :) Come kayak the Apostles with me as your guide in June [code Maddy25 for $50 off]
Swim more - Despite literally living in the Apostle Islands all summer with access to prime swimming conditions, I think I only went swimming twice? It’s one of those things that I always forget how much I love it until I’m doing it, and when I’m guiding I so often feel too busy to swim. With scaling back to focus on just a few trips, I’ll hopefully be able to enjoy my summer a little bit more and focus on writing.
don’t look away now (in case you missed it)
This Wednesday I published a mid-week essay on odd jobs I’ve had, and how working odd jobs in the tourism industry paved the way for me to work as a freelance outdoor/travel writer and photographer. On one hand the essay is very very much about that; on the other, it’s about how everything is political, and the people who tell me (often) “don’t talk about politics ever we came here for outdoor pictures”, and about the experiences I have that made me think the way I do. You can read the full essay here.
Small business spotlight✨ Lost Creek Adventures
Last summer, I worked as a guide at Lost Creek Adventures! Lost Creek runs guided trips out into the Apostle Islands and day trips to the sea caves nearby. I know all of the guides here, and would recommend any one of them wholeheartedly.
I’m often asked if there’s a way to request me as a guide— there is not! The only way to guarantee me as a guide is to join one of my overnight women’s paddling trips (keep scrolling!). That said I’ll likely still be hoping on a few weekend day and half day trips to guide over the summer as needed in the schedule, so there’s certainly a chance you’ll see me out there!
One cool thing Lost Creek Adventures is running is a beginner Whitewater Kayaking Course April 21-24; $595 includes all gear, food, lodging. This is a really great opportunity for anyone looking to get into a super cool new sport :)
Why being “cringe” is cool:
I’m here in defense of the girls posting get ready with me videos, and dancing for trends, and being silly online for fun. I’m here in defense of the girls with embarrassing outdoorsy blogs getting made fun of for sport by canoe bros. Firstly, because it takes a lot of bravery to be “cringe” online— to do something publicly because it’s fun and to not care that other people think it’s embarrassing. Opening yourself up to criticism is brave.
When I was learning Armenian, one of the foreign language teachers gave us the best advice I’d ever heard: the one thing that adults who become fluent in a foreign language have in common is that they were not afraid to be bad at it first. Or, if you will “cringe”.
Being “cringe” is productive. The unassailable ability to withstand embarrassment makes you the type of person who can learn as an adult and become really, really good at something. And in the terms of the internet, content, and art you really do have be “cringe” at something before you can be good at it. Before you can make seamless videos, you’ve gotta make some clunky ones. Before you develop a photo editing style, a voice for your blog, a writing style that hits, you are going to be cringey. It’s part of the process.
It’s one of the reasons I’ve left the blog I started in college, eight years ago, live online instead of deleting it. I think it’s important for people to see that we all start somewhere. I started out “cringe”— I’m still “cringe” sometimes.
And if you’re the person being called “cringe” online, don’t worry girl. The people calling you “cringe” could never.
overnight women’s paddling trips for 2025:
For summer 2025 I’ll be bringing back (and bringing more!) women’s paddling adventures with my friends at Chicas Abroad! I met the Chicas team while guiding in the San Juan Islands and had so much fun working for them that I decided to join the team.
for all of these trips, the code Maddy25 will get you $50 off! I make a small kickback at no additional cost to you:
June 24-29, 2025: Sea Kayaking in the Apostle Islands
Bringing back last years Apostle Islands sea kayaking adventure! I ran two of these last year and they were truly both so much fun— the first trip we had wild weather got paddle the Bear Island sea caves, some of my favorite in the park. The second trip the weather was… perfect? It was eerie beautiful and I honestly look back on it as one of my favorite trips of all time as a guide. These trips are always extra fun because of the people though :)
code Maddy25 for $50 off
August 6-10, 2025: San Juan Islands, Washington
When I first met the Chicas team, it was when I was a coastal kayaking guide in the San Juans! I was the sea kayaking guide for the sea kayaking portion of this exact trip, while Jocelyn took on the Chicas coordination and logistics portion with Chicas. I’m so stoked to be running this trip again, this time joining for the entirety of it, along with Jocelyn, who is so much fun! This is truly an awesome trip— come see orcas and wildlife and camp in one of the best places there is!!
code Maddy25 for $50 off
August 22-25, 2025: Boundary Waters, Minnesota
Come explore Minnesota’s BWCA, paddle into a remote BWCA lake, basecamp and hop on the Border Route Trail to beautiful, remote BWCA overlooks! Here, we’ll focus on practicing reading topographical maps and introductory canoe camping skills. This is a great trip to join if you’re a beginner paddler, or a more skilled canoe paddler looking to learn from experienced guides to set yourself up leading your friends in the future! This is a super small group, with me and another female guide along for the best possible hands on learning experience.
code Maddy25 for $50 off
Like the TC ideas
I’ll look forward to the solo short trip car camping write up. There are some great FB groups and blogs devoted to car and truck bed camping set-ups.