Exploring new trails and reconnecting with nature – that’s what it’s all about, right? There’s just something so rejuvenating about breathing in that fresh mountain air, feeling the crunch of the dirt path beneath your boots, and losing yourself in the sights and sounds of the great outdoors. We’re excited to share insider intel on the best Lookout Mountain hikes near Chattanooga, Tennessee. This stunning area is a nature lover’s dream, with miles of awe-inspiring trails winding through lush forests, past cascading waterfalls, and up to breathtaking overlooks.

Grab your hiking boots, pack a snack (or two), and explore the best hiking trails Lookout Mountain has to offer!

Glen Falls Hiking Trail

Difficulty Level: Easy 

Kicking off our list is the Glen Falls Trail – a short but sweet trail perfect for a leisurely stroll in nature. 

This 1.2-mile out-and-back trail meanders through a calming forest, treating you to the sights and sounds of several small waterfalls and flowing creeks. 

As you make your way along the trail, watch for the stone stairs that lead you through a door carved right into the rock. Once on the other side, you’ll be greeted by a beautiful view of the bridge and creek below. 

Sunset Rock via Point Park

Difficulty Level: Moderate 

If you’re in the mood for a slightly longer hike with jaw-dropping views, the Sunset Rock via Point Park trail is an absolute must. 

This moderate hike is a 3-mile out-and-back journey that will take you through steep metal-grated steps and connect you with the iconic Bluff Trail.

And let’s not forget about this hike’s grand finale—Sunset Rock. As the name suggests, this spot offers views of the Tennessee River and the surrounding valley, making it the perfect place to catch those golden hour hues as the sun dips below the horizon.

Sunset Rock Viewpoint

Difficulty Level: Easy

If you’re short on time but still want to soak in those incredible Sunset Rock vistas, we’ve got just the thing for you. The Sunset Rock Viewpoint trail is a quick 0.2-mile out-and-back that packs a serious punch when it comes to scenery.

This quick and easy route features a small parking lot and a trail of broad, flat stones that create a series of steps. In just 10 minutes, you’ll find yourself at the viewpoint, taking in those sweeping views that make Lookout Mountain special.

Point Park Loop

Difficulty Level: Moderate

Point Park Loop is calling your name if you’re in the mood for a leisurely stroll that still offers plenty of natural beauty. This 0.5-mile loop trail is the perfect way to stretch your legs and soak in the sights and sounds of Lookout Mountain. 

As you go around the loop, you’ll be treated to views of the valley below. And since this is a popular spot for walking, you’re bound to encounter fellow nature lovers along the way, making it the perfect place to swap trail stories and make new friends.

It’s a popular trail, especially on weekends, so consider visiting on a weekday for a quieter experience.

Ruby Falls

Difficulty Level: Easy

Okay, so technically, Ruby Falls isn’t a hiking trail. But this unique underground waterfall attraction is such an iconic Lookout Mountain experience we just have to include it! 

Ruby Falls is a paid waterfall attraction located in an underground cavern, and it’s definitely worth the visit! 

After gearing up with the provided accessories (think waterproof jackets and lighted helmets), you’ll follow your guide deep into the heart of Lookout Mountain, descending over 700 feet below the surface. The stunning 145-foot Ruby Falls waterfall is the main event, which cascades into a subterranean pool and stream. 

It’s such a cool (literally and figuratively!) adventure that takes you into the very belly of the mountain. Just be sure to wear shoes with good traction, as the cave floors can be slippery. 

J.C. Wilson Loop via the Guild Trail

Difficulty Level: Moderate

Last but certainly not least, we have the J.C. Wilson Loop via the Guild Trail. This 1.6-mile loop is perfect for those seeking a bit of a challenge and a chance to really immerse themselves in the great outdoors.

As you make your way along the trail, you’ll be treated to stunning rock formations and plenty of opportunities for rock climbing (for those feeling extra adventurous). And since this is a less-traveled route, you’ll have a better chance of spotting some of Lookout Mountain’s incredible wildlife along the way. 

Book Your Rustic Retreat Today!

Phew, that was quite the adventure, wasn’t it? But we’re just getting started! At Timberroot Rustic Retreats, we believe that the best way to experience the great outdoors truly is by staying in accommodations that are just as connected to nature as you are.

Our rustic vacation rentals are designed to provide you with all the comforts of home while allowing you to immerse yourself in the natural beauty that surrounds you fully. From cozy cabins in the woods to charming cottages with breathtaking mountain views, we have something to suit every adventurer’s taste.

So, what are you waiting for? Book your stay with us today and start planning your bucket list of amazing hikes! 


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wauhatchie woodlands

chattanooga, tn

Our flagship tiny cabin resort might be just a few minutes from downtown Chattanooga, but you’ll feel like you’re staying deep in the woods. Our tiny cabins sleep 4-6 guests between the bedroom and lofted sleeping area, and feature modern amenities, heating and air conditioning, full kitchens, and to top it all off, a private, outdoor hot tub. As an added bonus, most of our cabins are dog friendly, so your four legged friends can come along too.