Stand on Annapolis Street in late December and wait for the Budweiser Clydesdales, and you will wait a long time. The horses aren't coming. They never were. The parade everyone in West Annapolis half-remembers seeing happens a mile away, on a completely different street that just happens to share half its name.
That mix-up is not a small thing to get wrong if you live here. It means showing up on the wrong block for an event you've been looking forward to all year, while the one that actually belongs to your neighborhood, the one with your name on it, runs without you.
Two Districts Share A Name, Not An Address
The city of Annapolis draws a clean line between these two places, even if casual conversation doesn't. In its own business district guide, the city describes West Annapolis as a primary point of entry to Annapolis and a brisk walk to the city's vital center, renowned for colorful boutiques, antique stores and upscale services in its commercial core, with side streets that house the largest concentration of professional and healthcare provider offices in the city. That's the village built around Annapolis Street and Giddings Avenue.
Inner West Street is a different entry entirely. The same city page describes it as a dynamic blend of commercial, professional, cultural and residential elements, anchored by circuit and district courthouses, three high-end hotels, and a significant number of busy office buildings. That's the strip running toward Church Circle and downtown, closer to the State House than to Wardour.
Two districts, two commercial identities, one overlapping name. If you've ever told a friend to meet you "on West Street" and ended up in the wrong part of town, this is why.
Even The People Running The Parade Mix It Up
The confusion isn't just a resident problem. It shows up in how the event itself gets talked about by the people who organize it. John Mulberger, marketing director for Katcef Brothers, the Anheuser-Busch wholesaler that helps bring the horses to town, described the annual visit this way: "whether that's in West Annapolis, or on West Street, we see thousands of people come out", treating the two names as interchangeable in the same sentence.
They aren't interchangeable, at least not for where your feet need to be. The horses get hitched to the Budweiser wagon on Calvert Street, and trot up West Street, around Church Circle, down Franklin Street to return onto West Street for several loops. The event is organized by the Inner West Street Association, which along with Katcef Brothers arranges the meet and greet as the horses parade down Inner West Street and around Church Circle, timed to the day before the Military Bowl, in late December.
Even the West Annapolis Business Association's own site blurs the line. Its about page lists the group's yearly highlights as "several major social events a year, including the Oktoberfest and an annual visit from the Clydesdale horses," as if both happen on the same streets. One does. One doesn't.
| Event | Hosted By | Where | When |
|---|---|---|---|
| Oktoberfest | West Annapolis Business Association | Annapolis Street | Sunday, Sept. 27, 2026, 11 a.m.-4 p.m. |
| Miracle on West Street (Clydesdales) | Inner West Street Association and Katcef Brothers | Inner West Street and Church Circle | Day before the Military Bowl, late December |
The One That's Actually Yours
Oktoberfest is the real hometown event, the one that closes your own streets instead of someone else's. This year it lands on Sunday, September 27, 2026, from 11 a.m. to 4 p.m., and the association is partnering once again with RAR Brewing and Chessie's Wharf as the beer garden sponsor. Expect the usual formula: an ice-cold brew, bites from local restaurants and food trucks, and a chance to get a jump on holiday shopping from a rotating lineup of vendors.
It's the kind of event that only works because it happens on a street people already walk every day, not because it was built to draw a crowd from somewhere else.
A Second Calendar Nobody Mentions
Here's the part that surprises people who've lived here a while but never dug into it. Oktoberfest belongs to the Business Association, but Halloween belongs to a completely different organization. The West Annapolis Civic Association runs its own separate calendar for residents rather than merchants, and its fall centerpiece is smaller and quieter: free pizza and a costume contest to kick off an evening of trick-or-treating.
The same civic calendar carries the village through to December, when it hosts a holiday market with local vendors and a visit from Santa Claus, held the first Saturday in December from 11 a.m. to 6 p.m. in the parking lot at Giddings and Annapolis Streets. Two associations, two audiences, two calendars that overlap in season but not in sponsor. If you've only ever heard about Oktoberfest, you've been getting half the picture.
The Storefronts Filling In Around It
The dining scene along Annapolis Street has been adding to itself lately. Positano, a new addition, is described as adding to the growing dining scene in West Annapolis with a modern Italian menu. It runs from 11 a.m. daily, closing at 10 p.m. Sunday through Thursday and 11 p.m. on Friday and Saturday, with happy hour from 3 to 6 p.m. on weekdays featuring discounted house wine, draft beer, craft cocktails, and select menu items.
That's new. The anchors around it aren't. McNelly Optical has been fitted around four decades of practice, with Ed Marshall bringing 41 years of optical knowledge and craftsmanship to the family-owned independent opticians that have served the village long before Positano's ovens went in. Weems Creek Nursery School has been the neighborhood's preschool since Mary Ostrowski bought it in 2018, and she later founded The Drizzle Effect, a children's learning center, in 2024, adding a second stop to the same short stretch of storefronts. Great Harvest Bread Co. rounds out the food and beverage list the business association keeps for the village, one more name that's been baking bread here long enough that most residents don't think of it as new anymore.
None of this reads like a strip mall. It reads like a village that fills its own gaps rather than importing them, which tracks with how the city itself frames the district: a small commercial core doing a lot of the professional and personal-care work for the neighborhoods around it.
Knowing Which Street You're On
The point isn't that the Clydesdales don't matter to West Annapolis residents. Plenty of people who live on Annapolis Street will walk downtown in December to see them, the same way plenty of downtown residents will drive over for Oktoberfest in September. The point is knowing, without having to guess, which event is actually happening on your own block and which one requires a short trip somewhere else.
Oktoberfest is the one with your address on it. Everything else is a nice reason to leave the neighborhood for an afternoon and come back.
If you're weighing a move to a block like this one, where the calendar is layered enough that even the people running it occasionally mix up their own streets, that's the kind of detail worth having someone local walk you through before you commit to an offer. Brian Jacobs at Annapolis Fine Property has spent years sorting out exactly which traditions, streets, and associations belong to which corner of Annapolis, and is glad to talk through what that means for a specific block, not just a neighborhood name.
