Don't ask me why I took this picture, which is a heavily obscured view of Lake Mendota taken from the aptly, if unimaginatively, named Lake Mendota Drive in Shorewood Hills. This small community's best feature is its large inventory of beautiful homes dating from 1927, its year of incorporation. So why isn't there a single house in this picture? (There's one at the end of the long, curving driveway.) Perhaps I feared that I'd be mistaken for a Google 360 photographer and beaten within an inch of my life. Or, at a minimum, have my camera taken from me. I missed a defining picture of Shorewood Hills about a half mile west of this point. Two lakeshore homes side by side. One a McMansion built on the site of a teardown. The other a modest but well-kept home dating back to the village's early years. The smaller structure looks like a beach cottage in comparison.
In the past, I've always skirted Eagle Heights, a sprawling complex of mostly 2-story, UW student apartment buildings with a population of about 3,000 residents. No wonder it seems so much larger when you bike through it.
The J. F. Friedrick Inn & Conference Center, located along the lakeside bicycle/pedestrian path, used to be the site of UW-Madison SLIS's Basic Reference Summer Camp by the Lake. I taught this weeklong course three times but passed the baton four or five years ago. The windows of the 3rd-floor classroom to which I was assigned are obscured by the tree. This year, the course is being offered at the Pyle Center, which is great for the instructors as the FriedrickCenter is technologically challenged.
No, this bike trip wasn't a replay of the "Stopover in a Quiet Town" episode of the Twilight Zone. But you'd think, huh? Where'd everybody go? This photo was taken as I headed toward Memorial Union.
The razing of Ogg Hall. This picture has no sentimental value to me as I didn't attend UW. In fact, I never lived in a highrise dorm when I attended college, except for a 3-day freshman orientation at UB (the old, or what is now called the "South" campus) during the summer of 1968. 
Ugly buildings alert. This stretch of redevelopment along Regent Street has always struck me as cold, sterile, and off-putting.
(As you can see, it was clouding up at this point of my bike ride.)At this point, I headed in the opposite direction along the Southwest Commuter Trail, a veritable interstate highway of bike/pedestrian paths. (I vote for a Northwest Communter Trail, which would directly link Middleton and downtown Madison on an auto-free route.)
Ugly building alert, part 2. The Regent Apartments.
An artless shot taken in Nakoma, one of my favorite Madison neighborhoods, annexed by the City in 1931. This photograph does not do justice to a carefully planned layout of curvilinear (and now leafy) streets lined with beautiful homes in a variety in 1920s-era styles: Dutch Colonial, Tudor, English cottage, American colonial revival, etc.
Most residential neighborhoods -- those without restrictive covenants -- feature at least one home painted in a color that would look out of place even on a circus wagon. Here's an example found on the west side of Madison.
A 2006 assessment of the Westgate Mall is posted here. Working from a 1961 Madison City Directory, I once made a list of the original tenants of this originally unenclosed shopping center. Although I have misplaced -- or tossed -- the list, I recall it having the usual business mix for this type of mid-20th century retail development: grocery store, local department store, drug store, shoe store, cleaners, "5-&-10", women's & men's apparel, candy shop, appliance store, gift shop (more likely a "shoppe") etc.
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