Fall is now in full swing! I absolutely love this season. As evenings begin to cool and the sun’s heat becomes subdued during the day, something in the air feels crisp and comforting. Is there a more perfect time to hop in the car and go looking for some adventure!?
This packing guide will cover everything you should bring for a weekend away during the fall season. Want to do a little hiking? Need something casual for shopping? Eating a nice dinner out? I have you covered! Keeping in mind a weekend is just a few days, I’ve tried to pack items that are versatile, while still providing options for those last-minute changes of plan.
Outdoor Outfits
Since the weather is cooling down, opt for leggings rather than shorts. These leggings add a pop of color without being overbearing. They have pockets, which is great for keeping your phone protected when you need your hands free!
I have become obsessed with my quarter zip sweatshirt lately! The one I have is no longer in stock but this similar one comes at a great price point as well. Layers are important for fall weather, especially when you know you will be outdoors. Even if the forecast projects a high of relatively hot temperatures, the temperatures in the morning or in the shade will vary. That’s why I definitely recommend layers!
This green sweater is the perfect color for fall! It’s not super heavy so it is easy to throw on last-minute with some black leggings. I sized up to a medium (normally xs or small) because I wanted a baggy fit. My leggings have mesh panels and a fun print. How cute are these black snake print leggings with pockets!?
Any sneakers will do, but it does help to have some that are made for the outdoors; the soles will be a little more grooved to grip the terrain and keep you from slipping. In the photo above I’m also wearing this Beis Convertible Backpack (which I am obsessed with). I’ll talk more about that in a moment.
Casual Outfit
Okay, so this is really like a casual outfit + backup shirt. If you are just going to saunter around town or perhaps even do a little putt-putt like we did, having a casual but chic outfit will step up your look without much effort. I love this mustard colored cardigan for fall. And these woven slip-ons have quickly become a favorite pair of shoes.
Dressy Outfits
There’s not much I don’t like about a burnt orange midi-dress in the fall. Our sunny weather was perfect for these short sleeves, though I think a dress like this one with longer sleeves is perfect too. For walking sandals, these are my very favorite sandals of the season! They’re comfortable and don’t slide off. I think the white adds a nice contrast to all the darker neutrals we typically see for fall. After hiking the waterfalls, changed and freshened up at the B&B, then off we strolled through the old town of Hot Springs to learn about the famous bathhouses and shop the local boutiques. In the evening, we shared a dock-side dinner which was the perfect way to spend a sunset.
The Backup Outfit
I believe that you can still pack light and have space for a backup in case you change your mind or your plans! I chose a second dressy look with one of my favorite boho maxi dresses. My dress from Target is sold out, but here is a very similar style that is still available. These light camel boots are comfortable, though I recommend sizing up half a size to account for the pointed toe and socks. And last, but not least is the structured wide brim hat. I found this one on Amazon for under $20.
How to Pack Your Bags
Beis Dopp Kit for toiletries 
The wire top keeps an open structure. 
Beis Dopp Kit – bottom compartment 
Packing Clothes and Shoes
To pack efficiently, I do use the rolling method instead of just folding up my clothes – even dresses! Once I get to the place we’re staying, it’s nice to undo the dresses and hang them if possible. I like to keep my shoes separate from clothing by using the extra zipper side of the bag. I use a carry-on size with a hard case like this one.
Caleb was able to pack all his things in this weekender bag available on Amazon. I have had this bag a couple of years now and it’s one of my favorites because it is very spacious inside. It also has a separate zipper compartment at the bottom that we like to use for shoes or dirty laundry.
Packing Toiletries
You can see in the photos above I really love our Beis Dopp Kit in black. Caleb and I are both able to fit our toiletries for the weekend in this one little bag. I especially appreciate the bottom zipper compartment that runs the length of the bag. It fits at least 2 full-size hair care products! I brought dry shampoo, hair spray, along with all my skincare and of course, my Billie razor. This carrier is very compact and isn’t going to take up much real estate in your bag.
Packing Makeup
I have a square makeup case like this one, again in black. The best thing about this bag is that it has special dividers so that all your makeup can remain as organized as you like. Honestly, when I’m packing for a little weekend trip, I only bring essentials and a lot of my makeup stays home on my vanity. Whether you’re like me or you like to go big wherever you are, a travel case like this one will become your BFF.
Packing My Laptop and other Road Trip Items
For everything else I need to bring on the road, I use my Beis Everyday Convertible Backpack every time. For starters, the detailing of the canvas bag with the black crock accents just gets me. It’s so unique and but sleek! It’s very spacious inside, so I can easily fit my 13 in. laptop, a couple of books, and of course, snacks for the road! Additionally, this bag can be worn in multiple ways. I switched it from a tote to a backpack and carried essentials for us as we hiked each day. The placement of the straps is comfortable and the bag’s construction is durable. Cannot say enough good things about this backpack!
Did I miss anything? Feel free to ask any questions in the comments section. I’m happy to chat! I hope these tips are helpful and inspire you to [safely] plan your next fall road trip. The great outdoors or the next little historic town await you!