Hiking with my baby has become a wonderful way for us to explore nature and create lasting memories together. We are spending the summer in Montana so I’m reviewing the hiking trails that Parks and I explore from a perspective of hiking with a baby. One of our first hikes together was a beautiful 1.5-mile trail called Holbrook Overlook Trail in Whitefish, Montana.
Jump To…
- Holbrook Overlook Trail Overview
- Holbrook Overlook Trail Terrain
- Holbrook Overlook Trail Pros and Cons
- Conclusion

Holbrook Overlook Trail overview
The trailhead is located about 4 miles up Big Mountain Road. It’s part of the Whitefish Trail System.
Holbrook Overlook Trail was a rewarding and family-friendly trail. What sets this trail apart is that it starts and ends at the overlook itself, offering breathtaking views right from the beginning.

Holbrook Overlook Trail Terrain
Starting from the parking lot, we descended through a series of switchbacks to reach the starting point of the family loop, which spans approximately 0.9 miles. The trail treated us to stunning vistas of Whitefish Lake throughout the entire hike. While the downhill switchbacks provided an enjoyable descent, we were mindful that we would eventually have to make the ascent back up.

Approaching a trail fork, we faced a choice between the West and East Loops. During a conversation with fellow hikers who offered their insights, we learned that the West Loop was the more challenging and steepest option. Considering our intention to take it easy and ease into our hikes, we opted for the slightly shorter East Loop.
Further along the trail, we encountered another fork, this time with the option to take the East Loop or the East Loop Cut-off. Curiosity and a sense of adventure led us to continue on the outer East Loop, which we anticipated to be approximately 1.5 miles.
On our way back up, the switchbacks posed a nice challenge but were certainly manageable. I was able to make the entire climb back up while wearing Parks without taking a break. This was an easy trail that I recommend for families with kids of all ages.
Holbrook overlook trail Pros and Cons

I’ve already mentioned the stunning views from the overlook and throughout the hike. So that’s definitely a pro!
At one point, we came upon a family picking huckleberries. They all had buckets hanging around their neck by string or shoelaces and were enjoying the opportunity to fill them up. It almost looked like a competition with Dad as the toughest competitor. I picked a few Evergreen Huckleberries for myself and Parks and we went on our way. Considering the amazing views, the huckleberries were a bonus.
At the trailhead, there is a nice picnic area with a table and incredible views for visitors to enjoy a nice lunch. There’s no hiking required to access it, so you’re not committed to a hike if you are looking for a nice picnic spot.

As we immersed ourselves in the beauty of the setting, a minor downside was the presence of a major road below, which generated some traffic noise. While not ideal, it didn’t detract much from the overall experience.
Conclusion

Holbrook Overlook in Whitefish, Montana is a special trail. I liked that the overlook itself is the starting point and we’re still rewarded with panoramic views of Whitefish Lake throughout the entire hike. It’s family-friendly, no doubt, and it turned out to be a great place to find and pick huckleberries, which is a fun activity for kiddos.