As usual, Mr. Moore has outdone himself in capturing the oft-public golf experience in Boston.
I was flabbergasted and excited when I saw GW fully profiled, as I considered it my home-away-from-home course while living in Brookline and South Boston from 2005-2012 (Tedesco is 18 miles north of Southie, GW is about 5 miles SW). I've played GW roughly 25 times, in bad times and good, since about 2000. I've never teed it with Cob at GW, but that needs to be remedied soon...as we already spend too much time together at various MGA events.
As for the "Upper level" idea of Boston munis, I would argue that RonMon is accurate. Many cities have a good rota of munis within 5-10-15 miles of the city center, but there is often one flagship course with pedigree, leaving several other bastardized layouts to fight for the city funding scraps that fall off the showcase course's table.
Within 20 miles of Boston, with a northerly bent, I submit, in order of quality:
GW...well documented, today's crown jewel to be sure. 36 holes at GW and FP below would be a great day, and you probably would get more history and Boston experience out of it then TCC/Charles River or Winchester/Brae Burn, etc.
Franklin Park....the historical crown jewel, the 2nd oldest public course (Van Cordtland) in the US. Willie Campbell (original designer and pro), Georgina Campbell (Willie's wife and America's first female professional), Donald Ross (redesign architect), Bobby Jones (practiced here while at Harvard Law), Dedicated locals (who mowed holes in the morning and played in the afternoon when the course was closed in the 70s), and Tiger Woods (first tee clinic in the early 90s) have all played a part in its history. It's finally getting some city $ love in recent years, and it's as fun as ever. 6000y par 70, maybe $40 to play...TOTALLY recommend for a number of reasons.
South Shore...Hingham, MA...a Stiles course formerly private that is slowly undergoing restoration. This course is REALLY good, and only getting better. Not a tough test, there are some great holes out there with wild undulation rivaling any course in New England for movement and fairness. No better three hole stretch on any of these courses listed than #16 with its wonderful punchbowl green, #17 uphill long par three with the "Palmer tee" at 235 for the adventurous, and the 475y par 5 finisher with a stream fronting the green, and 5 feet of slope from back to front. Kudos for a classic Boston feature at #1, the 300y semi-blind opener with no place to lay up!
Gannon Muni....Lynn, MA is home to another great WPA clubhouse (not GW, but really neat as well) and Wayne Stiles layout. The course is home to some HUGE old trees, and fun, quirky holes are the norm. 6300y par 70, this course includes drivable par fours (2/6), massive elevation change (3/4/11/12/14), a completely blind par 3 of 230 (9), a wild short par four with 4-5 options on how to play (10), a C-shaped par four with incredibly playable angles (17), and a Highlands Links-esque 590y finisher! A real hidden gem, and if they lost about 3000 trees, we'd be talking George Wright quality.
Beverly Golf & Tennis...A formerly private club built by United Shoe Machinery Company, now run by the city of Beverly. Another Stiles course in the league with Gannon above, with fewer trees. More crazy quirky holes...long par fours with tiny greens (1/2), the most uphill par three I have ever seen with a 20 ft-tall flagstick (3), a 245y par three backed by the clubhouse (11), and the "wedding cake hole" (15), a drop shot par three played to a built-up green surrounded by bunkers. Just fun, cheap stuff with a pedigree!
Ponkapoag....long the runt of the litter, it has been recently refurbished, and I look forward to taking a look in the Spring. 2 courses, 18 Ross holes split between the two, with 9 of these closed for the past several years due to drainage problems. As far as I see it, they have fixed the water issues, and Silva's team has put it back together. Didn't get the Bethpage treatment and a US Open like the long-held rumor, but for locals, this will be just as good!
Olde Salem Greens....Stiles 9-holer in Salem, MA with incredible variety. 3 short par fours, a long, two-level angled par five, two par threes 250y blind downhill, and 145 semi-blind uphill. I have a soft spot as we practiced here in HS, and it's the closest public golf to my house (2 miles?)
Brookline GC...the former Putterham Meadows has notoriety as the parking lot for big TCC events, and the course borders TCC members #11 (composite #9). This is primarily Wayne Stiles, and for the most part the course suffers from uninteresting land, back and forth through a low-lying area criss-crossed by drainage ditches likely engineered to turn former wetland into a golf course. There is some fun undulation and rocky land nearest the clubhouse, but visitors tend to observe the greenest and best-looking holes right next to the clubhouse, and the shabbier more boring stuff visible only after you paid...
Sandy Burr...NW of Boston in Wayland...this is a Ross mail-in with a few noteworthy holes. The course borders a marsh so there is some fun interaction with the cattails along the edges, and the uphill 295y 9th is a real treat. Not on the level of any of the others above...maybe a tick better than Newton Comm, on the level of Brookline.
Newton Commonwealth....and old private Ross over near BC that sold several holes in the 1960s and today's public 18 plays about 5500 par 70. A bandbox to be sure, there are a couple 265y par fours, and #18 plays downhill 270 with a stream fronting the green with a sign on the tee that prohibits going for the green...the supremely confident tees up a driver and hopes nobody is looking! It's so far downhill that they used to run a rope tow on the 18th and operate a ski hill several decades ago. There are definitely a few fun holes here, and it's worth a play for the Ross mail-in archeologist.
There are others, of course, but I have only included those that have the architectural pedigree. Widow's Walk in Hingham has its fans, but Hurdzan was heavily neutered by environmental concerns, causing a result that is short and claustrophobic. Leo J. Martin is another (I have not played) that has a long history and a few devotees, but I have heard that it's only so-so. Mt. Hood in Melrose is not terrible, and has benefited from some recent work, but it's cramped and certainly behind the courses above. Braintree muni has a few good holes, but most are flat and back and forth, suffering from the same "cool holes near the clubhouse" syndrome as Brookline. Also noteworthy at Braintree is the 2-week Canada Goose-hunting season in November, but you might get more meat off of some of the deer flies drilling into your head while playing there in summer...