Landmarks abound at Race Brook – the stomping grounds of six Connecticut State Amateurs (including this past June), five Senior Amateurs and Six State Opens, among many other competitions. This summer’s Centennial celebration brought the venerable club into the spotlight – and it shined. You’d be hard pressed to find many layouts in the area with the playability, history, and beauty of Race Brook. It’s a classic spot.

Of course, the story – as it always seems to in golf – starts in Scotland. Pryde moved to the Connecticut area from Tayport in the late 90s – the 1890s, that is. A former Pro Shop assistant at Scotscraig Golf Club (which advertises itself as the 13th oldest in the world – join me in drooling while browsing its website), Pryde was quickly scooped up by Yale University to be its first ever golf coach. Pryde’s ‘rep in the area grew, and it was not long before his expertise was needed to design new golf courses, including Race Brook in 1912. As part of the club’s 100-year-old celebration in August, current members of Scotscraig were actually flown in from overseas.

Our group had a blast at Racebrook; the facilities, people, and course are all top notch. Here’s to another hundred.

Most Memorable Hole: Racebrook has natural beauty of all shapes and sizes – trees, water, rocks. The setting is most pastoral, however, on the 366-yard par-4 fourth hole, aptly known as “Red Barn.” That’s because abutting the tee box is – you guessed it – a red barn – which adds a unique touch to a gorgeous hole. I followed the course guidebook’s instructions and – as a “big hitter” – carried the bunker on the right side of the fairway, leaving me a short wedge to the green. I did not follow any guidebook’s strategies, however, for putting, and walked away with a bogey.

Most Challenging Hole: Number eight, a 422-yard par-4 gave me fits. A dog-leg right, you need to land your drive in the perfect spot – left side of the fairway – to have a look at the green on your second. Even so, you’re effectively staring at a tight, 180-yard approach to a well-guarded (by bunkers) stick.

Guru’s Tip: Race Brook is packed with friendly, helpful and classy staff, including General Manager Sean McLaughlin and Head Pro Paul Barnsley – so don’t be shy if you have questions. The warm atmosphere largely explains Race Brook’s staying power.

Most Memorable Hole: Hole #7, a 412 yard par 4 (pictured above) takes the prize, for its grand view from the tee-box. Your drive heads downward into a valley and an enormous barn-like house (with about eight garages) commands your attention in the distance. On a fall day with colorful leaves swirling, I can imagine #7 would be even more stunning.

Most Challenging Hole: “What the hell are you supposed to do on this one?” was the reaction from our group as we teed it up at the sixth hole, a 542 yard Par 5. About 300 yards out, the fairway turns to deep rough, and the hole elevates about 45 degrees before taking an extreme turn left. Getting home in two is simply not possible. The most difficult shot on this hole is your second shot – a “layup” – which needs to land on a narrow uphill fairway, tilting from right to left. Even if you’re in a good spot for your approach, you still can’t see the green until you’re about 50 yards out. A sneaky hidden greenside bunker on the right can take your frustration to another level.

The Bottom Line: While sometimes repetitive in layout and a bit out of date, the overall friendliness and country feel of Ridgefield is worth a short trip and more than worth the price of admission. But if you’re in New York City, New Jersey, or Long Island and determined to play in the Danbury-Ridgefield area, Richter Park should get the nod.

Guru’s Tip:  One of the better turkey burgers I have ever – yes, ever – had was at the turn at Ridgefield, which has a pleasantly surprising array of excellent food options at its upstairs restaurant. The turkey burger was fresh, juicy, tasty, and made me forget about my double bogey on nine.

Most Memorable Hole: Chances are you’ll leave Richter Park with a lot of favorite spots, but number five, a 174 yard par 3, is tough to forget.  Lining the hole is the gorgeous West Lake Reservoir, which you’ll have to clear to reach an elevated, two-tiered green, guarded by two large bunkers.  It’s a scene worth breaking out your camera for.

Most Challenging Hole: Richter’s “signature” hole is #12, and it’s also its most difficult.  The hole (a par 5) measures 527 from the tips, but unless you’ve got a pro’s power fade with incredible accuracy, a straight drive will put you in the woods, and not at the turn of the dogleg right.  Even if you hit a perfect tee shot, the chances of reaching this green in two are slim to none; first, because you can’t even see it from the middle of the fairway, and second because it’s engulfed by Boggs Pond.  If your approach drifts slightly to the right, you’re wet.  If you play it safe and stay left, you’d better be short, otherwise you’re in a bunker in back of the green with an impossible sand shot (one which you need to land on the green or else end up in the water). Once you’re on the green, do yourself a favor and take a moment to enjoy the tremendous views that surround you.

Guru’s Tip: Richter is on the pricey side, but does frequently offer specials.  Visit its website and make sure you sign up for email newsletters to stay posted.

The Bottom Line:  Richter Park deserves every accolade it receives.  It’s a terrific, challenging course set amongst an interesting, unusual backdrop.  While not exactly close to NYC (more than an hour’s drive), you won’t be let down if you make the trek.

While 17 is the most thrilling moment of a round at Brennan, chances are it won’t be its scariest.  This tight layout speaks to why the “Fore!” cry was introduced to the game – and when someone shouts that word at Brennan, you’d better duck…and quick (or, as noted above,  be wearing protective gear).

Narrow fairways are crammed between holes, the total of which measure just 5931 yards.  With amateurs spraying shots left and right, you’ll often find anywhere from 4-8 balls lying on any given fairway.  Furthermore, a bizzarely located putting green puts those who innocently want to practice their short game directly in the line of fire.

Brennan’s short, inconsistent layout is its biggest negative.  For example, a 228 yard par 3 (hole #13) is balanced by one that’s only 109 yards (#9).  There are three par 5′s, but the longest is just 485 yards.  You could show up to this course with four clubs and probably shoot a decent score – not much in the way of a challenge or variety.  And worse, two holes (12 and 14) feature gimmicky blind second shots to greens at the bottom of a hill.

Overall though, a day at Brennan is fun:  the course is nicely kept, #17 is a blast, and the pace of play won’t kill you (average of 4.5-5 hour rounds on weekends).  It’s affordable (just $49 for non-residents on weekends) and very easy to snag a tee-time on-line (in deep contrast to Sterling Farms).

Most Memorable Hole: #17 is clearly the winner, but second prize goes to the aforementioned 13th hole.  228 yards (longer with the pin in the back) is a tough distance for most amateurs and features a steep downhill elevation change.  The green is also enormous – not an easy two-putt.

Most Challenging Hole: I always have trouble with #5, a 368 yard par 4.  The fairway is tight and the green is elevated high above.  A powerful drive with some draw will put you in good position – but good luck gauging the slope and yardage on your approach.

Guru’s Tip: Zody’s 19th Hole is a solid restaurant and the halfway house at the turn makes excellent turkey sandwiches (REAL turkey, not processed).  They sell sandwiches in halves – and one of those is a good size and usually plenty.

The Bottom Line: Brennan doesn’t compare to Sterling Farms from a pure golf perspective, but it does provide an overall enjoyable experience.  So buckle your chin strap on and bring on the gallery.

**Note that there is currently a TON of construction on the course (presumably to improve the layout) – ditches and construction equipment come into play on the 17th fairway and green.

But with a little elbow grease*, you can find your way onto Sterling Farms. There are ways to beat the system and –  who knows – you might get lucky.  Is it worth all the hassle?  Yes.   Sterling Farms is quality.  Built on an old farm (hence the name), the landscape is serene and charming – barns and old farm buildings line the grounds. Despite the pastoral surroundings, Sterling is updated with golf’s modern amenities, including a recently renovated driving range, a well-stocked pro shop, and electric carts with GPS.  And with Sterling Farms’ steep inclines and elevation changes, you’re going to need the extra zip those carts provide.

*(see “Guru’s Tip” below for more on this)

The layout of the course is well thought-out and provides a challenge – particularly from the tips.  While not “long” by any standard (just 6486 yards from the back tees), Sterling will test your shot making skills.  There aren’t many water hazards, but lots of trees, slopes, and doglegs.

The course is well-manicured from tee-boxes to greens and takes advantage of its natural beauty as well, particularly on the back nine.  You’ll come across large boulders, deep woods, and the occasional pack of deer or wild turkeys.

The nit-picky negatives: pace of play is not as quick as it could be on weekends (especially with seemingly few tee-times) and the staff could be friendlier.

Most Memorable Hole: #2 (pictured above).  The first hole at Sterling Farms is its most boring:  a short, straight Par 4 (359 yards that plays about 330).  But just when you start questioning what the hype is all about (as well as wonder if wasting hours on Sterling’s website in an effort to land this tee-time was the best use of your Monday at work), you walk off the green and catch a glimpse of the 532 Yard Par 5 2nd Hole.   Right then, you know that Sterling Farms is no joke (although, if the above scenario did occur, your job might be).  It’s not so much that #2 is difficult, but more, intimidating.  From the tee box, it’s narrow, downhill and breathtaking (set way back from the photo above).  There’s usually a bit of a logjam on the 2nd tee, so you’ll probably have a gallery watching you.   And once you get down to the fairway, a wide creek about 100 yards from the green awaits your approach (as it turns out, there IS a lot of room for both your drive and approach, so don’t let the elements fool you).  It’s a pretty, well-designed hole which serves as your introduction to Sterling Farms.    Honorable mention goes to holes 4, 7, 10, 11, 12, 14, 16, and 18 – all of them fun and picturesque.

Most Difficult Hole: The fourth hole is the #1 handicap and deservedly so.  The green looks reachable directly from the tee-box to the left: all that’s standing between the flag and your manhood are a water hazard and a giant oak tree.  The smarter option, of course, is to lay up to the top of the dogleg, about 200 yards from the tee, straight out.  Go any further, and you’ll be in one of two large fairway bunkers.  Any shorter and the aforementioned oak tree blocks your approach.  Even if you land in the perfect spot, you’re still facing a potentially awkward stance and angle.

The Bottom Line: Play this course, figure out a way.  It’s a HUGE upgrade over any of the nearby Westchester Public Courses and puts its neighbor, Gaynor Brennan, to shame.

Guru’s Tip:  As much time as I’ve wasted dissecting how annoying Sterling Farms’ tee-time reservation system can be, it’s certainly not impossible to nab a tee-time there.  Obviously, option “A” is to get a Stamford Golf Permit somehow.  If you’re not a Stamford resident, be resourceful:  maybe you know someone that lives there and would be willing to hook a brother up?  It’s a picture ID, so that person needs to resemble you on some level. Your best bet WITHOUT a permit though is  - believe it or not – the day or two before you’d like to play.  To protect yourself, reserve a time at another course and then check Sterling’s website (frequently) on Thursdays, Fridays, and Saturdays. There are often last-minute cancellations – be ready to pounce.