Pros:
Challenging but fair technicality is the bottom line at Woodland Greens, creating the perfect complement to Highbridge's longer marathon courses. The host venue for Nate Doss' 2007 Pro Worlds victory, Highbridge features five primary courses on-site, plus a bonus campground course used primarily for glow rounds. The five courses on the hill are the main draw, with each one unique enough to showcase a different flavor of the richly diverse land. Woodland plays almost like a mini-Bear, the course it's situated closest to on the property. You'll find a good variety of left, right, and straight holes here, often playing through gaps that are tight, but far from unfair. Because of this, Woodland successfully avoids the "converted hiking path" pitfall that many other tight, technical courses fall prey to. The fairways were clearly designed for disc golf, preventing the frustration associated with holes that follow unnatural or impossible disc flight paths. Holes are short and reachable, with most playing 250 feet or less. That being said, midrange and putter control is a must, and most of the challenge here is mental. Keep it in the fairway, forget about that random, frustrating bogey, and you'll leave happy.
All of the courses at Highbridge are beautiful, and even the least scenic points on the property blow away most other routings by a country mile. Woodland doesn't provide a whole lot of scenery due to the tight woods you're playing through, but the setting is still green and idyllic enough to appreciate that you're not at your local park. This is a great course to play with kids, spouses, etc. who don't want to disc golf, but are just looking for a nice walk through the woods.
There's a single set of concrete tees on every hole throwing to Mach IIIs in good shape. These baskets were originally located on Bear, but the two courses were switched because Woodland gets a lot more traffic. A controversial decision, but the right move in my mind.
On the whole, Woodland receives similar maintenance care to Blueberry, which is the best at the complex. More often than not you'll find Woodland in acceptable shape, which is a small but critical victory at Highbridge.
Cons:
When you put aside all the drama and nonsense surrounding Highbridge, which are a con unto themselves for most (see other thoughts), there's really only one complaint that stands head and shoulders above the rest - Highbridge's inferior maintenance. It's a roll of the dice if the grass will be mowed on any given day, and tree trimming & rough control appear nonexistent. To make matters worse, Highbridge is approaching a relatively advanced age (14 years for most of the complex) where decisions should be made regarding tree removal, which will almost certainly never happen. When the courses are maintained, the level of maintenance is usually inversely correlated to its difficulty. You may come across an open fairway that's been mowed impeccably, only to play to a soggy green with waist-high grass. In all fairness to John, taking care of five courses with limited help is a rather difficult task, but that doesn't change the fact that unfinished mowing and trimming is a gigantic headache for us players. Depending on the status of the maintenance when you play, a course's rating could fluctuate by as many as two or more discs. Timing your visit to coincide with the intermittent mowing is just par for the course here. The Highbridge Hills - Wisconsin forum thread on this site is extremely helpful for providing detailed course condition updates.
There aren't many individually memorable holes here, which throws Woodland in sharp relief with the other four primary courses on the property. Most of the holes run together once you get in the swing of things, and depending on your play style and strengths you could find yourself either very frustrated or very bored.
In my experience, this is the buggiest course at Highbridge. You'll want to wear bug spray when you play all of them (I find standard "deep woods" 40% DEET works best), but you'll need to reapply a few times on Woodland to keep the insects at bay.
Routing is a little confusing for a course with such a small footprint. Stay peeled for the intermittent next tee signs and reference the map as necessary.
Other Thoughts:
With more twists and turns than a telenovela, the saga of Highbridge Hills has captivated golfers in the Upper Midwest for years. Regardless of where you fall between the two extremes of "John is a con artist" and "John is a harmless dolt whose reach exceeds his grasp", it's hard to visit here and not be charmed by the ramshackle enthusiasm of it all. Sure, it'd be great if a competent management team took over the complex, maintained it to perfection, and charged $20/day in greens fees to play what is probably the greatest collection of courses at a single site in the entire world. But where's the fun in that? Up here, disc golf still feels firmly tied to its DIY roots, as one man tries to hold it all together with chewing gum and string. Even as people (including myself) complain about the neglect of these world-class courses, it's important to remember that this version of Highbridge holds value as well. If you're looking for a true frolf adventure, Highbridge is the best place to find one. For now, it's best to enjoy what we have and hope for better days down the road.
Woodland seems to be the second-most popular course at the complex behind Blueberry, and it provides the perfect opportunity for a warm-up or cooldown round. Overall, the full 18 is far superior to the sum of its parts and, taken cohesively, makes for a pretty fun round. I'm told Woodland is also a spectacular course for glow golf, although I've never done it myself.