The Great American Road Trip

The Great American Road Trip

Earlier this year, I shared my plans to move into my car for a few months, so I could drive across Canada and back. For as long as I can remember, I have wanted to experiment with long-term travel; living out of a bag, moving at my own pace and staying in cities for as long (or as short) as I want. And I’ve always dreamt of exploring more of my country, visiting friends all along the way and, specifically, spending a good amount of time in the Maritime provinces. This is still a dream of mine – and is hopefully one I’ll be able to make a reality next year – but it’s not something I’ll be able to cross of my bucket list in 2016.

Since the time of writing that post, a number of circumstances have pushed back my potential departure date for that trip. First, of course, I had to recover from my surgery. I was discharged from physio in mid-June, so physically I’ve been ready to go since then. However, then both my dad and sister left for the summer, which resulted in my needing to stay at the house and take care of our family dogs. I have loved the quiet mornings with them, and all the walks around my childhood neighbourhood – but having to take care of them for 6+ weeks has meant not being able to hit the road for 6+ weeks.

The further my departure date was pushed back, the more I realized I wouldn’t be able to go on the road trip I had originally planned. And while I could be disappointed by that, instead I’ve decided to plan a different trip – one where I’ll still explore and hike, visit friends all along the way and end up in San Diego for FinCon. I’m calling it the Great American Road Trip! And it starts soon…

The American (Road Trip) Dream

Aside from my dream of driving across Canada, I’ve also had another dream develop over the past few years: driving around the U.S. and visiting all the wonderful friends I’ve made since starting this blog. With only seven weeks to play with, this time around, I won’t be able to visit everyone or even cross half the states off my list. But I am beyond thrilled to say I’ll get to explore a few places I’ve been dying to visit (like Montana, Colorado, Utah and California!), spend time with some of my best online friends, and see their states in a way I couldn’t have if I’d simply flown to them.

While in the past I’ve done a lot of “big city” travel, what I’m most looking forward to about this trip is that I’ll be able to explore everything outside of the cities. I want to see the small towns, the countryside, the mountains and the wildlife. I don’t care about city life, architecture, fancy coffee shops or restaurants. I want to see everything that surrounds it – and the best way to do that is by car.

The First Leg of the Trip

Technically, I do have a tentative route for all the states I’d like to drive through, but I’m hesitant to share it because I’m certain plans will change somewhere along the way – and that’s exciting! The biggest benefit of travelling solo is that I’ll have the freedom to go where I want, when I want, as well as stay somewhere as long as I want, or leave as quickly as I want. I also love knowing that friends will be able to suggest places to go (or skip). My friends Paul and Lisa have already done that for me, and shown me hundreds of photos from road trips they’ve done before.

As of right now, the only thing I have planned is to spend a few days in Montana by myself, then book it over to Minnesota so I can have a good visit with all my friends there. (Also, how is it that I have so many friends in Minnesota!?) Unless I decide to go through North Dakota (doubtful), I’ll drive through seven states in the first leg of this trip:

  1. Washington (driving through, will explore more on the way home)
  2. Idaho (just driving across the top)
  3. Montana
  4. Wyoming
  5. South Dakota
  6. Minnesota (stay with Anthony and Amy, hang with Jeff, Travis, Kayla and more!)
  7. Wisconsin (have frozen custard with Nate!)

From there, I’ll dip down a few states, then head back over to Colorado (where I’d like to hangout for a week) and make my way down to California. The only city I must arrive in by a certain date is San Diego, where I need to be by September 18th. Two girlfriends and I have rented a cottage there for three nights, before we head over to the hotel for FinCon (so excited to see them and relax before the conference!). After that, I want to drive up the California coast, visit some more family and friends, and then drive over to Bend, Oregon and head home from there.

Altogether, I estimate I’ll drive through 18 states in just seven weeks; that’s less than 3 days per state (and realistically, there will be many states I drive right through, so I can spend more time in others). It’s not the original trip I had planned, and I know living on the road for seven weeks won’t always be easy, but I am sooo excited to begin this adventure. Over the next few weeks, I’ll share more about how I’ve prepared for this trip (especially work-wise), what I’m packing in the car, and some ways I plan to save money and stay healthy on the road.

For now, I’m curious: is there anything I should see/do/avoid in the states I’ll be driving through in the first leg of this trip!?
  • Cait, you may find later (on hindsight) that it’ll be good that you have decided to take this shorter American trip rather than tackle the cross-Canada trip that you had originally planned. You’ll then perhaps be better prepared, through experience, to better enjoy that longer cross-Canada trip next year. You do plan on tackling that one next year, right? :-)

    Have fun, stay safe, and enjoy your travels.

    • Yes (to a shorter trip being a good start) and yes (to wanting to drive across Canada next year)! :)

  • I hope you get to spend a little time in San Diego outside of the conference! I lived there for a few years and can recommend a great taco shop called La Playa. It’s on Mission Blvd. in between Pacific Beach and Mission Beach and is a total hidden gem. Also, if you want a little light reading before you go, right now I’m about half way through Bill Bryson’s The Lost Continent which is a hilarious (although sometimes negative) account of his own road trip visiting small town America. Can’t wait to here more about it!

    • I will! I’m going to spend 3-4 days there before the conference starts and can’t wait to explore. Taco shop reco’s are always welcome, so thank you for that! I think we’re going to drive up to La Jolla one day, too. :)

      • Bird Rock Coffee Roasters in La Jolla is one of the best places ever. I highly suggest it! Grab some coffee and then go walk along the La Jolla cove and check out Children’s Beach to see tons of seals.

  • Sounds very exciting, Cait! Looking forward to seeing your on the road up dates – I’ve always loved the idea of a road trip (but I’d have to learn to drive!) through the States so I’m always interested in reading about other people’s!

    • Well then hopefully I can inspire you to learn how to drive, Meg! Or perhaps join me for a leg of the next road trip. ;)

      • It’s on the list for when we buy a house – no point in owning a car in Brighton as you can pretty much walk anywhere/parking is an absolute nightmare but we’ll be moving further down the coast when we actually are ready to buy a house because Brighton is stupidly expensive so will learn to drive then so we have backup for getting back into Brighton for work.

        I’m always happy to be a map reader/driver’s company though! :D

  • How amazing! I’d suggest the Oregon coast, but you’re going the other way for that. Have fun and enjoy every minute – we’ll look forward to hearing all about it when you’re back. Safe travels! x

    • I’ve driven about half of the Oregon Coast already, which is why I think I’ll move inland on the way home. One day, I’d love to do a road trip in the PNW so I can spend a good period of time exploring Oregon, Washington and BC. And I imagine I’ll write about the trip often, so stay tuned! :)

  • The only state on your list I’ve been to is Wisconsin. When I was a kid, we went to Wisconsin Dells which I’m sure is a total tourist trap nowadays, but I remember liking the Frank Lloyd Wright house.

    From WI, you could take a ferry ride across Lake Michigan. If you do that, drop me an email. I’d love to show you West Michigan. :-)

    • I don’t know if I’ll be able to make it to Michigan this time, but I’ll certainly reach out if I do! And the Frank Lloyd Wright house looks beautiful. :)

  • Get an annual national parks pass and make sure to see Yellowstone National Park and Grand Teton National Park in Wyoming/Montana!! With the pass you can stop in any national park for a low price!

    • Will definitely get an annual park pass! Adding Grand Teton to the list now. Thanks, Brooke! :)

  • WOW this sounds a great plan, well being Italian I am not right person for travel suggestion in the US, but I can say that I loved my American holiday in Michigan, I’m still dreaming about giant lake Michigan… I’m so curious about to read your adventures!!! I’m sure you’ll enjoy IT!!!

  • A South Dakotan here – glad to see you will be going through our little state! If you have time, consider stopping in Spearfish for some beautiful hiking and waterfalls. There’s not much to see in the middle of the state, but that’s alright because the speed limit is 80 mph :). If you find yourself going through Watertown, SD and get hungry, Guadalajara Mexican Restaurant has some of the BEST food in the state. Your road trip sounds like a blast!

  • The world’s largest ball of twine is almost on your way from SD to Minneapolis. The lady in the museum was super-nice and it won’t take long.

    There’s also Pipestone National Monument, which has a gorgeous short hike and is fun to explore.

    For American kitsch, you can’t beat Wall Drug in South Dakota. Get some fudge and browse all the random junk. It’s better people-watching than the fair.

    • WHOA! Pipestone looks cool! And my friend Lisa suggested I check out Wall Drug, haha. I’ll have to make a pit stop there ;)

  • While you are in Oregon consider Crater Lake, The Painted Hills and the John Day Fossil Beds. All are within driving distance of Bend.

    • Thanks, Stacey! Crater Lake was already on the list, but the others look amazing! I’ll definitely stop at both!

  • Wisconsin is THE BEST state in my opinion! ;) Friendly people, beautiful scenery and really good food! :)

    If you will be in the Madison area, and are a fan of architecture, you should really check out Frank Lloyd Wright’s Taliesin or House on the Rock in Spring Green, WI.

    If you come to the Milwaukee area, be sure to visit the lakefront! There are a number of different parks and beaches you can stop by depending on what you like to do and being on Lake Michigan feels like being at the ocean! Milwaukee also has several great museums (Art Museum is right on the lake) and you can do fun stuff like take a boat trip or rent a kayak to paddle down the Milwaukee River. If you come in the fall, just a little north and west of the city is a large cathedral on Holy Hill. You can climb to the top of the cathedral tower and see the changing leaves in four counties, it is beautiful! There is so much more in the state, but those are things I’ve done and enjoyed. Enjoy your visit! :)

    • Oh my gosh, thank you for all the suggestions, Kate! I’ll be driving through both Madison and Milwaukee, so will be sure to visit the lakefront. I’ll probably also find a place to camp in that area for a night. Thank you again!

      • I also highly recommend Madison! There are so many places to check out, but some options include the terrace on the lakefront, Marigold Kitchen for breakfast and Graze for dinner, the Saturday farmer’s market, the capitol and State St at night time. You can also get as many fried cheese curds as your heart desires :)

        • Fried cheese curds!? Oh my gosh, I don’t know if my stomach would like that, but it sounds amazing haha.

  • Yay exciting! We have only driven through the eastern part of the US but I would say if there is anything you can do to set up your phone to video off the dash for a bit that might be cool. You will want to see some of the scenery but you won’t be able to stop all of the time to take pictures and you have to focus on driving so that way you can capture some of the sights. Some areas that you are going to be driving through are going to be pretty awesome and while memory is great you might want to document as well. Have a great time and stay safe!!

    • Oh yea, that’s a neat idea, Sarah! I might also have to borrow my dad’s GoPro for this trip. I mean… when in Rome, right? :)

  • Hi Cait! If you’re driving Hwy 2 through northern ID and MT, Kootenai Falls is a neat spot, right before you get to Libby, MT. My parents live in Marion and love having visitors, if you need a place to stay! And you can’t go wrong with a trip up through Glacier. Take the FREE bus up the Going-to-the-Sun Highway, so much better than driving yourself! Hwy 93 from Canadian Border all the way to Salmon Idaho is my favorite drive and so beautiful. Also the drive along the Seeley-Swan (Hwy 83) is amazing, the hike to Holland Falls at Holland Lake is also one of my favorites!
    If you’re headed to eastern Minnesota come visit my current town, Stillwater!! The St. Croix river is a fun place to explore and if you need a place to stay, we have an extra room (and good breakfast!!)
    Have Fun on your trip!!!!

    • Oh wow, Kootenai Falls looks beautiful, Amy! I don’t think I’ll go quite that north, though, but will certainly keep that in mind. And I’ll definitely let you know if I’m going to pass Stillwater! :)

  • So neat! Fellow Canadian living just outside San Francisco here. This is probably weird, but I have a guest room you are welcome to use on your way back home if you like, as long as you don’t mind a cat! I recently found your blog and really enjoy it.

    • Not weird at all! I think it’s amazing so many people are open to having visitors stop through. I try to do the same for my travelling friends. I’m not sure if I’m going to stop in SF yet, but will certainly reach out – even if only for a coffee or something – if I do! Thanks, Calee! :)

  • I would definitely recommend a national park pass.
    Glacier in Montana is stunning. As is the little bit of Colorado I have seen.
    Enjoy yourself!

    • Ugh, I don’t think I’ll be going that far north… but now you’re all making me wish I was! Haha. :)

  • I appreciate your flexibility–that’s so essential to staying content when life throws us curveballs. I’m not sure if this falls under “city life,” but my sister runs the Northwest Film Forum in Seattle which has lots of special events surrounding independent films and cultural topics. Whatever you do, I’m sure you’ll have a blast!

    • Oh, that sounds awesome! I’ve skipped Seattle, the last few times I’ve driven past it, but do think I’ll make a point of stopping in on my way home. :)

  • Let us know when you have meetups! Please visit Denver/ Boulder, CO and I’ll come say ‘Hi!!!’.

    • I wasn’t going to plan any, but I’ll be spending a week in that area, so maybe coffee!? :)

  • If you have a chance to drive up the Oregon Coast I promise you won’t regret it. Our coast is stunning and completely worth the time. If you stop in Portland, grab coffee at Stumptown and VooDoo donuts for the road! Drive safe!

    • I’ve driven about half of it already! Was only going to skip it, because there are so many places inland that I want to see. And I’ve done both of those things in Portland, but will definitely be picking up some Stumptown beans on the way home. They are my all-time fave. :)

  • I long to see the American West and I so look forward to doing it when my children are older. There is so much to see – your trip sounds wonderful. I wish I did that when I was young and unencumbered!

    • You’re so sweet, Gwen! I don’t think I’ll be driving through Iowa at all, but I’ll let you know if plans change :)

  • I live in Colorado. If you get the all parks pass, it works for Rocky Mountain National Park.
    I believe one of the entrances to the park (Rt 34) will be closed by then, but you can still get there through Lyons. The Elk may be bugling by then – this is a surreal thing. The entrances to the park are adjacent to the town of Estes park. Lots of shops etc.. cute. Longs Peak is in RMNP and is the only 14,000 feel high mountain north of I70. (there are 52 in CO) It is also the peak on the back of the Colorado state quarter. It will be too late for you to climb, but always beautiful to see. Email me if you want any other Northern Colorado tips (where to hike, etc)

    • Ahhh, thank you so much, Becky! I think I am the MOST excited for Colorado. May be in touch, as I get closer to. :)

  • Your trip sounds like so much fun Cait! I am in Southern California in the Orange County area. I would love to meet up with you for a cup of coffee when you are near my neck of the woods :)

  • Definitely don’t skip driving up or down the California Coast, especially around Big Sur. Don’t be tempted by the quicker drive on the 5, it is so ugly LOL. The sea life you can see in CA is amazing, Moss Landing near Monterey is home to sea lions, harbor seals, and sea otters! Enjoy your travels!

  • I’m so jealous. I’ve always wanted to have the freedom to travel the states but fear has held me back. I think you have given me some courage to maybe start out small. California is a beautiful state and you will find many gorgeous places to travel; Big Sur, Monterey, Carmel, Mt. Tamalpais in Marin County, the redwoods up north, Yosemite. Just so many places. I hope you have a wonderful experience and see many places and meet many friends.

    • Thank you so much, Cheryl! I’m so excited to spend time along the coast, on my way home, so thank you for all the wonderful recommendations. And I can’t say my younger self would’ve done this trip, but I’m certainly glad to do it now. :)

  • I’m sure all your friends in Minnesota have probably mentioned but there are some Laura Ingalls Wilder sites in that area if that’s up your alley!

  • We should definitely grab coffee if you find yourself in San Francisco again! Your trip sounds amazing and I know you’ll have a blast :)

    • I’ll definitely be driving through – maybe staying 1 night! Will keep you posted :)

  • Have a great trip!
    I like that you were able to make alternate plans when the first trip was postponed. In the past i have just scrapped plans altogether when they didn’t work out and i was never happy with that. The idea of rolling it into a doable alternative plan never occurred to me! Seems obvious now though! Haha!
    As i live in BC i have no suggestions for your trip!
    Have fun. Drive safe.

  • Well I don’t know anything about the states your going to. I lived in Maine for the first 17 years of my life and have spent the rest in Florida. But, it sounds like an awesome trip and I can’t wait to see you FinCon.

  • I’ve grown up going to Bend nearly every year and it’s an awesome place! There’s Lava Lands, which has lots of lava rock from the lava flow and an awesome view on the butte) and a beautiful waterfall just out of town (and for some reason I can’t remember the name of the waterfall at all). And while you’re in OR or WA I highly recommend eating at McMenamins. There’s one in Bend, but many more north as well. Most of them are old historic buildings that two brothers renovated and turned into Pubs and Hotels. Plus if you go during haply hour (I don’t drink myself, so I get their strawberry lemonade), you can get a lot of food for really cheap (like $2-4 an item, still decent sized).

    • I don’t drink either, so strawberry lemonade it is! Thanks for all the suggestions, Sereina! :)

  • I’m definitely jealous of your upcoming trip, Cait. I’m suffering from a major case of wanderlust this week and just want to get out and see some new things.

    Take lots of pictures (safely – not while driving) and share them here on the blog for us!

  • I have always wanted to do exactly the trips that you seem to have the desire to do, but so far have not been able to commit that much time to do it. I can’t wait to hear about how you got everything organized to make this happen. Even if it isn’t the original plan, it will be so awesome!

    • I know, that’s exactly why I’m taking advantage of the time/freedom now… because I’ve never had it before, and who knows when I’ll have it again! Seize the day :)

  • So excited for you Cait!! Can’t wait to hear all about it and see all the photos you take along the way! Hopefully will see you next summer, maybe. :) We may be planning a trip to the west coast of Newfoundland next summer to Gros Morne and area.

  • The National Parks pass also gets you free admission to all our national monuments and forests as well as all Corps of Engineer campgrounds. My pass is different from yours but I think yours will also get you 50% off camping in most of them that are NOT run by concessionaires. If you drive south along the Mississippi River, or any river the Corps has dammed, you’ll find lots of campgrounds. In the SW states there’s also free camping on most Bureau of Land Management properties.

  • I forgot to ask if you will be stopping in Montana to visit Josh & Ryan, the Minimalists?

    And to tell you, if your bring a jug into Wall Drug, they will fill it with ice water for free. Offering that is how they became famous in the first place.

    • I would love that but don’t think they have any idea who I am, haha. So cool about the free ice water! I know I want to make a pit stop there :)

  • It all sounds so exciting whatever you do. Being in England I can only imagine what is to come for you on your trip but I share the positivity.

  • San Diego is the best, though I am quite biased as a native. Some must sees are the San Diego Zoo (world famous…the pandas are amazing), Balboa Park (there is always a free museum on Tuesdays and some of them are free all the time, also just a great place to walk around/hang out), Coronado Island (visit the Hotel Del Coronado…one of the 1000 places to see before you die! Super cute small beach town, lovely shops and beautiful houses and a great beach to just hang out at), I noticed you mentioned La Jolla, Warwicks stationary store is amazing there! If you are a beer fan, there’s tons of great craft beer in SD, and soooooo much great coffee (Bird Rock, Communal Coffee, and Coffee and Tea Collective are some of my faves!)

    Enjoy your trip!

    • Ahhhhh, thank you thank you thank you for this list! I know my friends and I will come back to it, when we get there. And I’m definitely going to Coronado Island!

  • I’ve lived in or around San Diego my entire life, and my top restaurant recommendation (if you like seafood) is the Pacific Beach Fish Shop on Garnet Avenue.

    I also want to add that I’m new to your blog, but I love it! You feel like a friend, and I am inspired to start a One Year Shopping Ban, because I need some help curbing my spending.


    • Hi Jamie! *waves* So glad you’re here and enjoying the blog so far. Don’t feel like you have to start with a full year, but maybe set some guidelines for 30-90 days. And I really appreciate the restaurant reco! I do, indeed, like seafood :)

  • Bend is one of my most favourite places ever!
    Hike up Pilot Butte.
    Go on the free Deschutes Brewery Tour (and get to sample their goods!)
    Float down the Deschutes River on a tube

    We were there 12 months ago and we talk weekly about getting back there some time soon (from New Zealand!)

    • Oh my goodness, that must’ve been quite a trip for you! Did you specifically go to the US to go there? Or was it just one stop? :)

      • When you live at the bottom of the South Pacific, a 12hr flight ain’t no big deal ;-)
        We road tripped from San Francisco to Seattle via Tahoe, the Redwoods, Bend, Portland etc over a three week period.
        Bend, for us, was just one of those places we’re we felt immediately at home.
        I can not wait to explore more of the States though.

        • Oh my goodness, now I’m even more excited to get there! And I have to wait two more months! Haha. Thanks for sharing with me, Michelle :)

  • On your journey from Colorado to San Diego, don’t miss Sedona, Arizona. Drive down the 89 A from Flagstaff. It’s a switch back road and the scenary is amazing! You will take many pictures. And say “wow” over and over.

    • Yes yes yes, my friend Lisa showed me pics from her road trip and it looked amaaaaazing! :)

  • Oh yay! You’re coming to Milwaukee! We have the BEST custard! You’ll love visiting here!

  • Have a great trip Cait! I agree with Superhero that I have some serious wanderlust right now too – and we will be doing a similar trip next fall! Looking forward to hearing your updates (and sorry – we’re on the East coast!) Be safe!

  • Cait, I’m so excited you will visit my state of Wisconsin. I hope you love it as much as we all do. Frozen custard is delightful, make sure to bring a cooler to keep some Wisconsin cheese with you, as well. Make sure to try some Collectivo coffee, as well. If you have time either Door County or Lake Geneva are both wonderful, as are the Wisconsin Dells. There are so many things to do here, including seeing a Green Bay Packer game. It’s truly a state with a lot of gems that most people don’t realize. However, you’d have to stay a few weeks! Enjoy yourself! It sounds like an amazing trip.

    • Mmm, thank you for the coffee reco! I think I’ll only be there for a couple days, but am so excited to explore! Anything with the word “lake” in it piques my interest ;)

  • Your trip sounds amazing, Cait! I’m envious!

    I have to second the National Parks – we were in Yellowstone and Grand Tetons last year and just returned from Rocky Mountain – all are fantastic places to visit with so much to see (I am particularly fond of Yellowstone for it’s amazing variety). Also, in the Black Hills of South Dakota, stop in at Custer State Park if you have time – Needles Highway is fun to drive, the wildlife loop has some very friendly mules, the hike to Harney Peak is fun (the highest between the Rockies and the Pyreneese), and there is a nice bike trail along the old railroad bed.

    And, I’m in Iowa too, so if your route changes and you drive through Des Moines…we have a camper! Have a wonderful trip! Looking forward to reading about it.

    • Wow, who knew there was so much to do/see in South Dakota!? Hehe. And to think, I nearly went through North Dakota instead. Can’t do that! Thanks for all the suggestions, Amanda :)

  • Are you going through Missoula, MT? It’s a must see! I live in Missoula, and there are many local breweries, many more local restaurants, and the downtown scene is awesome, even during the week nights, where you can even see people surfing the river here!

    • Yes yes yes! I’m definitely stopping in for a night or two :) so cool about being able to surf on the river!

      • Awesome! Hike the M if you can for best views of the city! Hit up the farmer’s market under the Higgins Street bridge if you are here on a Saturday Morning!

  • You would love the hiking along the California Coast, especially in Big Sur. There are beautiful camp grounds there too.

  • make sure that air conditioner is tuned up. Take some tools in case you break down. An extra alternator belt is a good idea. Not sure how old your car is or how new.

  • Have a great trip.
    South Dakota is one of the most beautiful places I have ever visited. I would go back there in a heartbeat!

  • South Dakota is beautiful. There is a dramatic change in landscape when you cross the Missouri River in the middle of the state. Take a quick stop in Mitchell at the Corn Palace.

  • Hi .. have a great trip! Thanks for letting us all into your life. I really enjoy your posts, and am planning some long journeys myself.

  • California is a very beautiful state and highly recommended. I lived there 19 years and wish I had explored more then. Just a little note, the coast isn’t the best way to travel, even when you are trying to see everything. It can be very slow going…I would try to see Big Sur if you can, but you’d want to take highways from San Diego, and then head over to the coast. Also, San Francisco is about the coolest place ever.

  • Cait, In California don’t miss Point Reyes Seashore! It’s beautiful. And if you decide to deviate slightly away from the coast, consider passing through beautiful Northern California wine country, full of adorable towns and great spots for camping.

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