Immediately when you arrive Crestline, you can feel the small town charm and clearly, the San Bernardino mountains and Lake Gregory are the stars of the show. The first time I visited Lake Gregory was in 2023. After many trips to the lakes surrounding our mountain resort towns, including Big Bear Lake, Green Valley Lake and Lake Arrowhead, I decided this lake by far is the best one for everyone! Shortly after my first visit, I purchased the Cabin by Lake Gregory.

Lake Activities
I love Lake Gregory because it is a public lake. Unlike Lake Arrowhead, you can fish, launch your own boat, rent canoes, kayaks and paddle boards, plus enjoy the hiking trail loops and dog parks that surround the lake! You will want to visit a few times to experience the weather year round and all the different activities you can enjoy depending if it is spring, summer, fall or winter. Unsurprisingly, the peace and crisp mountain air is certainly a pleasant constant no matter when you visit!

Hang Gliding and Paragliding
If you are an outdoor enthusiast, you’ll love the Lake Gregory area, not only for all the fun you can have on and around the lake, but also for its close proximity to the world-class hang gliding and paragliding launch. If you’re rated, you can schedule a tandem ride with a professional or you can just be a spectator. The views are incredible and at 5,262’ elevation, this launch site is the highest and offers the longest flights of all!

Heart Rock Trail
If gliding is not your thing, and you rather be grounded, the Heart Rock Trail is just 5 minutes from the property and is truly unique to other trails in the area. It’s a moderately easy and popular hike that follows a creek, which leads to a beautiful 20 foot waterfall featuring a heart shaped hole on the cliff.

Skypark at Santa’s Village
With a total size of 677, 982 acres, the San Bernardino National Forest is too big to tackle in just one visit, and Skypark deserves its own trip, especially during the holidays! This year round attraction is known throughout the world as the premier outdoor adventure theme park. From mountain biking, zip lining and ice skating to puppet shows, magic shows and live entertainment, there is nothing else to do but have a blast!

Wine Tasting at Sycamore Ranch
After adventuring for a couple of days outside, you might want to switch it up, and if you’re into wine and hard cider tastings, plan a visit to Richard and Elizabeth Krumwiede’s Sycamore Ranch Vineyard & Winery before you head back to your Cabin by Lake Gregory. The story of how they became award winning winemakers is an inspiring one and the wine proves to be worth the trip every time. The 3.5 acre estate is magical and the perfect site for outdoor tastings. Reservations are available for Fridays 1pm & 3pm and Saturday and Sunday 11am, 1pm and 3pm. Call (909)338-1725 to make one!

Rim of the World Highway
You won’t want to forget making a few stops along the Rim of the World highway to take in those breathtaking panoramic west coast views. There are convenient viewing points (and even an observation deck) where you can safely park your vehicle and step out for a photo or two. The drive around the mountains is impressive so don’t forget to catch the sunset on one of your evenings around town!

Lake Arrowhead Village
While you are up in the San Bernardino mountains, you may want to do a little shopping and dining. Lake Arrowhead Village is a fun visit, especially if you want to get to know the broader area. The lake is also very beautiful and there is a one-hour narrated boat tour on the Arrowhead Queen that is offered from Memorial Day weekend through Labor Day weekend. You’ll learn about the history of the lake and how it became a popular shooting location for Hollywood and a second home to many celebrities. Before you leave, pop in to the one-of-a-kind boutiques and grab some souvenirs from your lake trip!