A Long Weekend in Colorado

Long Weekend in Colorado

Already planning another trip back to this beautiful state, so I thought I’d document this one. 🙂 If there’s one thing I want to start by saying, it’s this – treat yourself to a fall trip. Go somewhere where the foliage is changing and the weather is crisp and you can truly enjoy the season. We did New England last year and Colorado this year. Soon enough I’ll have a list of destinations for your consideration, maybe. 

Colorado was a great choice for a fall trip (although I would recommend a late September/early October trip as opposed to our mid-October). We still had gorgeous weather and views, but we just missed peak leaf-changing. Before we get into it, just know this was my first time in Colorado and I have tons more to see – but this was just my experience 🙂 

Our itinerary was:

  • Day 1: Fly into Denver and drive straight to Vail (we had a late flight)
  • Day 2: Vail
  • Day 3: Vail → Denver with a stop in Idaho Springs
  • Day 4: Red Rocks, Boulder, Denver
  • Day 5: Denver 

Some general and money-saving tips:

  • Rent a car. We used a cheap car rental and it did the trick, but having a car will definitely be the easiest way to explore the state and see what you want to see. (Another tip: be conscious of the car you rent depending on where you’re going. Get 4-wheel drive if you’re in the mountains, dealing with snow, etc. We had a Ford Escape and it was perfectly fine!)
  • If you go to Vail in the fall (their off-season), their parking lots are free! NICE!
  • As with most vacations, I recommend stopping at a grocery store and grabbing breakfast foods, snacks, drinks for the apartment, etc. IT ALL ADDS UP 
  • Download the AllTrails app if you’re interested in hiking – people add reviews of hikes (oftentimes helpful if you’re unsure about trail conditions, weather, etc.), photos, and descriptions so you can choose the right one!
  • If you have accommodation in Denver after flying in, you can take the train to downtown Denver from the airport for about $10. Likely beats the price of an Uber if you’re not traveling with a group!


I was a little hesitant to go to Vail in the fall because it’s known for their winter season (skiing, snowboarding, Christmas decorations, etc.) but we absolutely loved it. The hikes in town were beautiful, OPEN (a problem I later ran into in Switzerland during their off-season), and it wasn’t incredibly crowded. 

We stayed in this Airbnb which was about a 5-10 min drive from most places of interest in Vail. It was cute and comfortable and had a Nespresso machine : ) 

Our goal in Vail was to explore the village and do a hike or two. We ended up choosing the Booth Falls trail and loved it. If you’re in decent shape, the hike is not very difficult and I believe we spent about only three-four hours with a few stops and a long relaxing break at the top.

Long Weekend in Colorado

Seeing it was my first time in Colorado, I was VERY appreciative of this hike. I was also wildly unexperienced and brought my parka because it was 40 degrees when we first starting hiking. I took it off after walking for 10 minutes and had to carry it with me the whole time lol. Learn from me.

Long Weekend in Colorado

One of the best parts of Colorado (I concluded, after my first visit) is finishing a hike and grabbing beers at a brewery. If you’re even somewhat familiar with the state, I’m sure you’re aware the place is just filled to the brim with craft breweries. Knowing it was in a cute area in the village, we went to Vail Brewing Company, stalked diners to steal their outside table, and got some flights of beer. Sipping beers outside in the sun in late October was one of the highlights of our trip.

That brings me to another best part of Colorado (maybe I’ll make a list at the end of this)– you can sit outside, comfortably, when it’s 50 degrees. The sun just HAS YOUR BACK. Chicago could never!

After relaxing at our Airbnb for a bit, we walked around Vail Village until we were ready to eat. This was our last full day in town and I am absolutely sure I’ll back. Place rocks.

– Hiking
– Exploring Vail Village
– Skiing/snowboarding (if you visit in the winter)

The Little Diner – We went here for a hefty breakfast before our hike and loved it. Reasonable prices, delicious food, and a little bit of a wait but that’s when you know it’s good
Vail Brewing Co – Get yourself a flight and an outside table and people-watch. It’s magical
Vendetta’s Italian Restaurant – If you’re in the mood for a cozy restaurant with good pizza, come here. It’s an older, homey restaurant that was perfect for a more casual dinner, which was what we were in the mood for.

I know there’s a lot more fancy and ritzy places in Vail for me to visit at some point of my life, but we’re taking it a day at a time, ok? 

Idaho Springs

Long Weekend in Colorado

We only spent a few hours here, but it’s an easy stop on the way from Vail to Denver. The St. Mary’s Glacier hike came highly recommended, and it was amazing– not very long, but very rewarding. It was the perfect hike to do after our longer hike the day before. (The photo below was taken about 10 min into the hike!) I’ll let the pictures speak for themselves though.

Long Weekend in Colorado

Long Weekend in Colorado

After our hike, we went into town, which is very small and known as looking like a little mining town. It was adorable 🙂 

Walk around, grab some lunch and beers at Westbound and Down Brewing Company or Tommyknocker Brewery & Pub – we went to both lol. Also I heard Smokin’ Yards BBQ was phenomenal, but I ruin everyone’s trip because I don’t eat meat so I can’t speak for it myself.

Then get on the road!


Long Weekend in Colorado

A lot of people kind of skip through Denver when traveling to Colorado, but Kyle has friends there and we were interested in seeing the city, so we spent a decent amount of time there.

After writing this, it looks like we MOSTLY ate and drank (ideal) while hitting a couple areas with shopping/sights. If you’re into museums and zoos, there’s tons of that, but I prefer to up my daily walking until at least 6 miles and stuff myself with food and beer in between! And stuff we did!

I’ve included all the spots we hit below, but exploring LoDo and RiNo (I am basically a Denverite) are good starting points, as well as LoHi, which is a bit more residential but has Avanti, Denver Beer Co., and much more. 

Many people recommended hitting Red Rocks whether or not a concert is playing. We explored and got our steps in for the day, and now I’m sure my next trip will include a concert 😍 Such a cool venue.

Long Weekend in Colorado

Long Weekend in Colorado

All in all, Denver is a cool city. Hard to compare to Chicago (much more different than I thought it would be) but I’m excited to go back and explore some more neighborhoods. And continue to cross off my list of breweries.

Larimer Street – A cute and trendy street with string lights and boutiques
Dairy Block – Trendy! They call it a ‘micro-district,’ kind of similar to Larimer Street (shops, restaurants, string lights, etc.)
– Union Station – Even Denver’s main transportation hub is cute. We grabbed a coffee here before exploring the city
Red Rocks Park & Amphitheatre – I mean. You know what it is

Food & Drinks
Avanti – It’s like a food hall but nicer and with an outdoor space. People come here to drink too – what a concept! I got an arepa and I think about it often
The Woods – This is a rooftop bar that is a part of RiNo’s “The Source Hotel and Market Hall,” another interesting concept with shops, restaurants, and a hotel. Great views of the city – we went twice : )
Denver Biscuit Co. – There’s a reason it’s always crowded. YUM. Not super vegetarian friendly but they were accommodating to my requests
Denver Beer Co. – A Denver staple, great outdoor space, did I mention I love that I can drink beer outside in 50 degree weather there?
The Wynkoop – A brewery in LoDo. Huge and has pool tables and good beer
Uncle – We’re pretty spoiled when it comes to ramen, tbh, so it’s no Wasabi BUT it was still very enjoyable. Get the edamame appetizer if you like spicy food!
City O City – Our stop for a hearty vegetarian breakfast. Loved it and very veg/vegan friendly : )
Ironton Distillery – Phenomenal outdoor space with firepits


Long Weekend in Colorado

We drove here for half a day and I’m so glad we did. I loved this town, although I have to admit I’m partial to college towns (I am that person). We spent most of our time strolling along Pearl Street, dipping in and out of the cute little shops 😊

Then we drove up to Lost Gulch Overlook, admiring the views the whole way up, and hanging up there while trying not to fall down from the wind lol. It’s a BEAUTIFUL spot, though.

If you do one thing, though, go to Avery Brewing Co. Just realllly good beer and very friendly people and outdoor activities and dogs everywhere. It was phenomenal. 

IN CONCLUSION: I hope any of that was remotely helpful if you’re planning on going to Colorado, and if you weren’t, I hope I’ve convinced you it’s worth your time. I’m already looking into flights to go back 🙂


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