My Omaha Obsession
05/04/2026
Today we have a small but interesting case study: 311 South Happy Hollow Boulevard, situated upon Lots 22 and 23, Block 6 of Evanston Addition (those tidy numerals so beloved of municipal order). Lot 23 is to the north, and has always been undeveloped--a tucked-in green scape, concealed by foliage. A lilac bush, trees. We loved the secrecy. Had there been a 309 South Happy Hollow Boulevard at some point? No, not that I could find. The absence of a 309 South Happy Hollow Boulevard is precisely the sort of small civic mystery that invites more speculation than it strictly deserves—and yet, one cannot resist! The principal structure on Lot 22, attributed to George Heidkamp and dated, with a certain postwar optimism, to 1947, stands as a contributing structure within the Dundee / Happy Hollow Historic District. It is, in short, the sort of house that does not shout, but is noticed nonetheless. She is said to be of the Prairie School but I see a MCM brick Colonial with an addition above the garage and many lovely additions in the rear.
Enter, then, the recent architectural intervention: a carriage house erected following a building permit secured in October 2024, to the not inconsiderable sum of $66,240. The property has since undergone a transformation that is as much narrative as it is architectural.
The carriage house—ah, that most romantic of secondary structures—has been executed with a commendable discretion and insinuates itself into the inviting speculation of all passersby: was it always there? The answer, delightfully, is no. But it behaves as though it might have been, which is infinitely more important in this case. The new carriage house looks to be from the 1920s. My goodness, is this carriage house possibly older than the actual house? The structure accommodates a two-car garage, only reached by the alley (we live for alleys) and yet hints at loftier ambitions: an office, perhaps; an art studio for the temperamentally inclined; a guest room for the occasional houseguest who must be both welcomed and contained; even the faint whiff of rental possibilities. Or, if one prefers, a secret retreat—every proper house, after all, ought to harbor at least one. I call ours my pouting room.
What distinguishes this carriage house is not novelty but manners. It is cohesive with its surroundings and possessed of that elusive quality so rarely achieved in contemporary building: historical plausibility. It is the windows. It is the gables. The clean brick and mortar matches up nicely with 307 South Happy Hollow Boulevard, the lovely home to the north, allegedly built in 1927. It is the height of the structure. It is the set back. It is the nonchalance--almost with its back turned. One cannot help but observe that the new carriage house, for all its admirable discretion, exhibits a faintly ambivalent posture toward the public realm. It has, as it were, turned its back—an architectural gesture of studied indifference that is deeply appealing. There is something wonderfully self-possessed about a structure that declines to perform for the street.
(One small obsessive criticism--How shall one put it without sounding ungrateful?—the presence of a front-facing door introduces a note of hesitation. One rather wishes it had committed fully to its aloofness. To turn one’s back is a statement; to half-turn, a compromise. Had it been omitted, the structure might have achieved a purer, more Delicious Defiance: a building entirely uninterested in being approached, admired, or even understood. As it stands, it remains charming and approachable. I know I am being a Miss Cassette on this point.)
Who was the architect of this carriage house? Was this builder designed? Was it owner designed? The garden, too, has been coaxed into collaboration, softening edges and blurring timelines until the ensemble reads as a single, if slightly enigmatic, composition. It is growing as we speak. It will only become more lovely over time. One is tempted to conclude—though not without a raised eyebrow—that the success of 311 South Happy Hollow Boulevard lies precisely in its refusal to declare itself new. It improves, it even amuses. And in a neighborhood where history is both currency and performance, such restraint is not merely admirable; it is, quite possibly, the most stylish gesture of all.
Brava, Miss Carriage House and thank you, Homeowners, for creating something of beauty and a true delight. We love your new carriage house.
04/09/2026
We've got a new buddy on the block. Omaha Bagel Company has planted their sign at 5423 Leavenworth Street. The Little House That Could had served as the favorite corner Cottage grocery store for the residents of Dundee-Elmwood decades ago and has hosted various successful enterprises since. Welcome Omaha Bagel Co.!
Please click the link below for the original investigation from 2020. It includes the full history of the building, families and businesses.
https://myomahaobsession.com/2020/04/06/mysteries-of-omaha-5423-leavenworth-street/
03/30/2026
Alexander Payne's 1996 film Citizen Ruth, starring Laura Dern, gave a compelling, sunless reflection of Omaha. I remember seeing it at the Dundee Theater--fun to see each shot, look for the familiar sights and ultimately face a darkened mirror. (A compliment.) Here is a 1996 still of Laura strolling west on the sidewalk in front of the old Dundee Hardware Plus. It was stationed on the southeast corner of 50th and Underwood Avenue at 4949. The cinematographer’s camera was also situated there and caught a glimpse of 1990s Omaha. I do miss that row of awnings across the way.
The Baskin-Robbins ice cream shop offered 31 flavors. You may have heard. I have documented it—my hands-down favorite of the chain. Someone we knew was always working there. I was in love with that drinking fountain. Isn't that weird? It had the iciest water in town and emitted a funny, soothing hum and occasional clunk from its hot-to-the-touch Brutalist bubbler. It was located next to Godfather's Pizza—a steady hit with us tweens and teens, although decidedly not as cool as the Old Market location. The Underwood Bar, a fixture in the area, remains at 4918 to this day. I don't remember what was next door to the east but I'm sure one of you does.
Blue Line Coffee, an essential, took over my beloved Baskin-Robbins. Sometimes I wish I could still smell the bleach and sweet, old milk combo. The incredible Dario’s Brasserie at 4920 Underwood Avenue was in the once Godfather’s bay for many good years. Such a shame to lose that great restaurant in 2022. Underwood Bar, as mentioned, still holding it down. Ooh De Lally at 4916 Underwood upstairs, was once the location of Mark’s Bistro. I appreciate this angle as it reveals the historic foursquare house integrated into the restaurant's Mid-century Modern front. The Better Homes and Gardens Real Estate office is now at 4949 Underwood Avenue, once location of the Dundee Hardware Plus.
Concept derived from Set-Jetter and Film Oblivion combined with my current update.
I hope you all have a beautiful week.
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