USA
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Kentucky Road Trip From Chicago: The Perfect 3 Day Weekend Itinerary
3 Days, 2 Nights Louisville, Kentucky ~5.5 hrs from Chicago 100+ Stone Arches in RRG Best Spring to Fall Dog Friendly: Partial. KENTUCKY ROAD TRIP FROM CHICAGO Quick Facts: Route Chicago, Illinois to Louisville, Kentucky Drive Time About 5.5 hours one way Best Time to Visit Spring through fall for hiking, year round for Louisville…
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3 Day Rocky Mountain National Park Itinerary from Estes Park
3 Day Itinerary | Rocky Mountain National Park, Colorado | ~14 miles hiked | Timed Entry + Bear Lake Road Reservation Required | Not Pet Friendly on Trail Days If you have more than a single day for Rocky Mountain National Park, this is the itinerary we would build. Three days based out of Estes…
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Cottonwood Pass Colorado: A Continental Divide Stop at 12,126 Ft
Cottonwood Pass sits right on Cottonwood Pass Road between Crested Butte and Buena Vista, and if you are already driving through, we highly recommend making the stop. We made this stop on our way home from our Crested Butte trip, and it ended up being one of the best unplanned parts of the whole trip. Sweeping views of…
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Sky Pond Hike in Rocky Mountain National Park Guide
The Sky Pond hike in Rocky Mountain National Park is the kind of hiking adventure you think about for weeks afterward. It is rated hard on AllTrails, and it was the longest hike we had done, which made finishing it feel like a real accomplishment. The hike climbs a vertical rock scramble beside a waterfall,…
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Wisconsin Fall Foliage Day Trip from Chicago: 3 Best Stops
1 Day Kettle Moraine + Holy Hill, WI About 2.5 hours from Chicago Best in Fall Wisconsin Fall Foliage Road Trip Quick Facts Location Campbellsport and Hubertus, Wisconsin Drive from Chicago About 2.5 hours to Kettle Moraine Northern Unit Best Time to Visit Fall, mid October for peak color Total Hiking Distance About 3.5 miles…
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The Perfect Fall Weekend Road Trip: Galena IL and Dubuque IA (2 Day Itinerary)
2 Days Galena, IL + Dubuque, IA About 2.5 hours from Chicago Best in Fall Quick Facts Location Galena, Illinois and Dubuque, Iowa Drive from Chicago About 2.5 hours via U.S. 20 Best Time to Visit Fall, September through November Where We Stayed Irish Cottage Inn and Suites Budget Level Budget friendly Crowds Moderate, busier…
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First Time in Crested Butte Colorado: The Complete 3 Day Dog Friendly Wildflower Season Itinerary
3 Days Crested Butte, CO ~5 hours from Denver Best Late June to Mid July Quick Facts: Crested Butte First Timer’s Itinerary Location Crested Butte, Colorado Best Time to Visit Late June through July for wildflowers Where We Stayed Nordic Inn, Mt. Crested Butte Signature Hike Scarp Ridge Loop (Trails 419/421), 3.9 miles, 1,430 ft…
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Scarp Ridge Loop near Crested Butte: 10 Best Tips and 1 Mistake to Avoid
The Scarp Ridge Loop near Crested Butte ended up being the highlight of our entire trip, and fittingly, our anniversary too. We always try to do something epic to celebrate. Last year it was standing at the top of Pikes Peak during our Colorado Springs trip, and the year before that we were in Quebec…
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Crawford State Park Camping Near Ouray: The Ultimate Dog Friendly Guide (2026)
Crawford State Park is the dog friendly camping stop you do not want to skip if you are road tripping between Ouray and Black Canyon of the Gunnison National Park. We stayed here after finishing the Ouray Perimeter Trail, and it turned out to be one of our favorite camping nights in Colorado: lakeside views,…
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3 Epic Days in Dog Friendly Gatlinburg: The Ultimate Smoky Mountains Itinerary
4 Days Gatlinburg, TN Great Smoky Mountains ~10 hr from Chicago Best Late Spring to Fall Dog Friendly: Yes — Tira Approved Dog Friendly Gatlinburg Quick Facts: Location Gatlinburg, Tennessee Drive from Chicago ~10 hours via I-75 S Best Time to Visit Late spring through fall (May to October) Where We Stayed Vrbo dog friendly…