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Weekend Guide to the Major Cities in Colorado

Colorado Springs I Denver I Boulder 

Hi Friends!

My first trip to Colorado was made just this past June, 2020. After hiking through Yosemite twice, I realized how much I love to hike and be surrounded by nature and mountains. So, I started to think of other states and National Parks I wanted to visit after that. Colorado, was at the top of my list. 

My boyfriend, Tim and I decided to head out for a spontaneous, safe, socially distant trip in June for a Thursday to Sunday trip. Being cooped up during this pandemic and both with far more free time on our hands due to it, decided we needed to get out. With safety and convenience in mind, we decided to drive. All I can say is that this was slightly regretted at 3am in the pitch black of the night, eyes red from exhaustion as we both stared at the yellow lines passing us on the road, never ending. But hey, we made it. The drive was long and tiresome for only 2 people to accomplish, (Shoutout to Tim for taking the bulk of the drives lol). We were thankful though, because we could drive ourselves anywhere and everywhere once in Colorado. Being able to have our own car was very convenient and we never had to worry about Ubers/Lyft or rental cars.  

There are so many amazing things about Colorado, but, one of the coolest things was how close the major cities are from one another, and that all of them are completely surrounded by mountains and incredible views. The drives were beautiful, with mountains situated everywhere you looked. Through each drive we were presented a new view and different town/city. The craziest part is that Colorado Springs to Denver is only an hour and a half drive, then, if you want to head from Denver to Boulder it’s only a 30 minute drive! We couldn’t believe this. We ended up stopping in Denver two or three times since it was so close to our hotel in Boulder. This makes the trip very fun and expands your list of things to do. 

If you’re feeling cooped up during this pandemic or know you want to plan a trip to Colorado in the future, I definitely urge you to use this guide for help and inspiration. I’ve compiled a few things that we did on our trip that I would recommend to anyone, especially for a first trip to Colorado. Below, I’ll break up the three major cities to travel to in Colorado – Colorado Springs, Denver & Boulder. 

Here is your guide to Colorado’s major cities for a long weekend trip:


  • Driving Plan: We started driving Wednesday night and arrived in Colorado Springs Thursday afternoon. We left on Sunday afternoon and arrived home by Monday at sunrise. 
  • Time: Drive from Milwaukee to Colorado Spring was about 15 ½ hours. 

Our Tentative Plan:

*Now with this plan, it’s exactly what I said – tentative. We played it by ear for certain things and unfortunately COVID held us back from seeing a few places, but not a crazy amount. A lot of things were open! But, for example, we really wanted to go to a distillery in Denver, but many were not doing any tours due to COVID. So, there was a bit of free time that I wish we filled with more, but overall, I was very happy with our trip and saw so much in these cities. Feel free to follow a similar plan or make your own based on the “Things To Do” list provided in this blog! 

Day 1 – Thursday:

  • Arrive in Colorado Springs at 1pm
  • Horseback ride at Garden of the Gods
  • Dinner

Day 2 – Friday:

  • Garden of the Gods morning hike
  • Drive to Denver (1 ½ hour drive) 
  • Drive through the city
  • Dinner in Denver 
  • Drive to Boulder

Day 3 – Saturday:

  • Brunch in Boulder
  • 29th Street Shopping 
  • Rocky Mountains hiking 
  • Dinner 

Day 4 – Sunday:

  • Checkout of hotel 
  • Drive to Denver 
  • Lambrier Street in Denver
  • Denver Biscuit Company
  • Drive back home

Colorado Springs To – Do: 

  • Garden of the Gods hiking
    • This is a must do in Colorado Springs. Garden of the Gods is the town’s most popular spot and incredibly unique. This Nature Center is made out of red, jagged, sandstone formations and is truly “God like.”
    • The hikes are relatively easy here since they are all paved by the main entrance and not too inclined.
  • Garden of the Gods horseback riding
    • I HIGHLY recommend this for incredible views of Garden of the Gods and if you’re obsessed with horses like I am. This was such an amazing experience being able to ride these horses through the trails. For me, this was a bucket list moment so I was very happy and excited. 
    • Ride at Academy Riding Stables: To ride the horses for an hour was $65 per person. We were given pretty quick instruction on how to ride the horses and then taken on the trail. Riding them was super simple and very fun. I recommend booking the 5pm “sunset” ride to get the best views of the mountains as the sun comes down. Academy Riding Stables made this experience very memorable. 
    • Location: 4 El Paso Blvd, Colorado Springs, CO 80904
Academy Riding Stables
  • Dinner at Paravicini’s Italian Bistro
    • We were recommended this Italian place by a few locals and it was very tasty! Timmy and I have had extremely authentic and homemade Italian pasta in Little Italy in Boston, so to say the least, our pasta expectations since then have been very high. This Italian wasn’t as authentic or delicious as Little Italy’s but it was very good and most definitely left us full and satisfied. The portions were very large too so you will for sure have leftovers to take home or you can even share!
    • Location: 2802 W Colorado Ave, Colorado Springs, CO 80904

Denver To – Do:

  • Walk around the city
    • Denver was a really cool city that I wish I had made more time to discover. I could feel that there was so much the city had to offer and if it hadn’t been down pouring the day we drove through, I would have loved to discover more. I highly recommend taking a drive throughout the city or parking and taking a walk. 
  • Larimer Street
    • This is a must see spot and one of my favorite areas in the city. Larimer street is one of the oldest and most historic blocks in Denver. They close off the block from cars and have restaurants and shops lining the street. There is outdoor seating all on the road and strung up lights overhead from beginning to end on the block. It is extremely cute and I recommend at least walking through it, if not stopping for a meal.
  • Denver Biscuit Company & Fat Sully’s New York Pizza
    • This. Was. Amazing. Tim and I had heard about Denver Biscuit Company and were wanting to go so bad. They are known for their homemade biscuits and yummy biscuit concoctions. Get there early because sit down spots book up fast. If that happens, you can always order at their walk-up window out front. They are also known to have amazing cinnamon rolls which I was freaking out for, but unfortunately they were all out when we got there. Come early!
    • We ordered the DBC Club which is the biscuit covered in chipotle sauce, as well as The Franklin which is the one with gravy smothered all over it. We added egg for good measure.
    • The biscuits are served in conjunction with Fat Sully’s New York Pizza. This pizza is really good! It’s a large, thin slice and can be ordered at the walk-up window in front of the restaurant. 
    • Location: There are a few locations in Denver. The one we went to is listed here: 3237 E Colfax Ave, Denver, CO 80206
DBC Club
  • Distillery:
    • Do a distillery tour if they’re open! They weren’t for us but tours may open up in the next few months. This is a great way to spend time in the city.
  • Mexican dinner at Rio Grande
    • This is a really yummy Mexican restaurant in downtown Denver. The salsa is amazing (similar to Uncle Julio’s – if you’re from WI you know) and the plates are fairly large. Tim and I shared the shrimp fajitas and they were so good. The tortillas were very floury and authentic that I even took some home for later.
    • Location: 1525 Blake St, Denver, CO 80202

Boulder To – Do:

  • Enjoy the drive heading north from Denver to Boulder.
    • The coolest thing about Colorado to me, was how close all of these major cities are. They are one straight shot from each other heading north, with Denver and Boulder only being a 30 minute drive from each other! Enjoy the beautiful views on this drive. Boulder is full of mountains, and as you get closer to the town, you enter a wide view of the mountains laid out in front of you and Boulder.
  • Brunch at The Buff:
    • This is a must. Hands down one of the best breakfasts I’ve ever had – and some of the fastest service. This place is apparently very popular and the best brunch place in Boulder as said from our hotel’s staff. Tim and I both got a skillet drenched in queso and a spicy sauce and it was to die for.
  • 29th Street shopping
    • This was a great way to fill up some time in Boulder and was surrounded with incredible views. All of Boulder is bordered by mountains, as is this beautiful, fully outdoor shopping center. The shops here are nicer, mid-range priced stores such as West Elm, Anthropologie, Altar’d State, Lulu Lemon, Madewell, Eddie Bauer, Nordstrom Rack, etc. Take a walk around the paved shopping center, grab lunch and enjoy the incredible views.
  • Rock Mountains National Park
    • Of course I save the best for last! I planned for this hike since Tim and I decided we wanted to go to Colorado. The Rocky Mountains are absolutely breathtaking and we only scratched the surface of all it has to offer.  
    • The Drive in: The drive in was unforgettable. We set off on our drive through the mountains heading towards the National Park. As we got closer, the mountains started to increase in height and the drive began to get windy. Soon, in the distance, we saw it – the first, massive mountain directly centered with the road we drove on, with the whitest of snow on the tip, just barely peeking through the clouds. It was beautiful. I was yelling in excitement. This view took my breath away, and as it got closer, it continued to. Soon, more white tipped mountains appeared as we drove closer and closer. The best part was driving through these mountains and entering a small town, which we later found out was Estes Park. This was a little town with touristy shops and restaurants and a very small-town, getaway feel. We were obsessed. The drive into the mountains continued to be beautiful and Tim and I debated if the drive in was more beautiful than Yosemite’s drive in – we settled on a no-questions-asked, yes. 
  • Rocky Mountains Continued…..
    • Time: 1 ½ hour drive from Boulder to Rocky Mountains. So fast and easy!
    • Hike: The main thing I wanted to see on this hike was lakes. So, we did the Bear Lake Corridor Trails hike. This trail consists of 4 lakes on your way, Nymph lake, Dream lake, Emerald lake and Lake Haiyaha. This hike was fairly easy and in my eyes the perfect combination of challenge and enjoyment. It was roughly 1.8 miles long one way and 10,110 feet in elevation.
    • READ: Look into the reservations for the park! This messed up our day a lot. We were supposed to go on an all day hike but little did we know that the park has specific time slots you have to reserve days in advance to go into the park at. Of course, all were booked for Saturday and Sunday. After my slight melt down, I called multiple numbers and found out that if you come after 5pm you don’t need a reservation. Obviously, this was not the day we were hoping for but we ended up doing it and were very happy with the decision! We got sunset views and cool temperatures to hike in. Everything worked out just fine for us but keep this in mind and reserve your time slot at least a few days in advance.
Nymph Lake
Dream Lake
Emerald Lake


As much as I don’t recommend the 15+ hour drive we did from Milwaukee to Colorado, I can say that it was very nice to have our own car to take us wherever we wanted to go. With that being said though, you could definitely fly and rent a car if you’re further out. Just be prepared for the miles you will be adding on since there is a lot to drive to and see in Colorado. 

Where to stay:

Hotwire: Tim and I stayed at a hotel in Colorado Springs as well as Boulder, both booked through Hotwire. We have chosen Hotwire for almost all of our trips because we get the cheapest hotel rates guaranteed. They normally are less expensive than Airbnb as well (Once you total up cleaning fees at checkout which are crazy expensive on Airbnb!). To hear more about Hotwire and what it is, checkout my NYC Travel Guide.

I am already excited to plan more trips to Colorado in the future! I feel like after seeing the major towns and cities, I know what I like and dislike. For example, Colorado Springs wasn’t exactly what I was expecting. Well, I guess I didn’t really have any expectations going into it, but, there were things I liked and didn’t like. One surprise to me was that the town of Colorado Springs was a bit more run down than I thought, smaller and very jam packed. I also know now though, that I want to discover more of Denver and see specific parts of Colorado that were recommended to us by locals. 

Traveling is a learning experience. Not everything goes perfectly or according to plan. You learn about what you could have planned better for, what you may like and dislike about a place, how well you travel with your partner or friend and what you want to see in the future. That’s why I love traveling so much. There is so much to learn, so much knowledge to gain and eye opening experiences that can only be made by getting out of your bubble and putting yourself somewhere you haven’t been.

– Kat

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Katerina Haros - Mindful Living Company - Professional Photography


You can call me Kat! I'm a Milwaukee native, always looking for something new to check out, whether that be in MKE or across the world. Follow my blog and social for all things travel, inspiration, lifestyle and living mindfully.

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