Late Summer in Downtown Cañon City: The Abbey News, a New Rooftop, and What's Open on Main

If you have lived here more than a year or two, your late-September default probably included a drive out East Highway 50 with a picnic blanket, a few folding chairs, and a plan to spend an afternoon on the lawn at the Winery at Holy Cross Abbey. That afternoon isn't happening this year, and it may not happen next year either. What is happening, quietly, is a shift in where downtown Cañon City gathers when the light gets long.

The one-sentence version of this summer: the west end of Main Street finally works again, one of the region's oldest anchors is stepping back, and a new rooftop is doing more business at sunset than anything else on Royal Gorge Boulevard. Everything below is what that actually looks like on the ground.

The Abbey news, and what it means for late September

After 25 years of winemaking in Cañon City, the Winery at Holy Cross Abbey may soon close. Since it opened to the public a quarter century ago, the wine-making operation at the historic monastery has won over 1,200 medals and awards in international competitions. But now its owner, Larry Oddo, plans to retire. The property is on the market, and the outcome depends on whether a buyer steps forward.

The immediate consequence for locals is on the calendar. This year, the winery is canceling its Annual Harvest Fest, usually held the last weekend of September. "Unless something changes, we simply will not have the wine or staffing to pull it off," Oddo said. If he can't find a buyer, the winery will shut down at the end of September.

This is the twenty-third year the community had penciled in that last-September weekend at 3011 East Highway 50. It was free, it drew people from Salida and Colorado Springs, and it functioned as the closing bracket of the outdoor season. That bracket is missing from the 2026 calendar.

Two things are worth registering here. First, the Abbey wines have carried some weight beyond the region. Local wine was chosen last year as the first from Colorado to be available at a national park, and is currently on the wine list at Yellowstone National Park. Second, if you were planning to bring visitors through the tasting room this fall, do it in August. September is uncertain.

Main Street exists again

The other big shift is that the west end of Main is finally a street. The city has a particularly long downtown area for a city of about 17,000 residents, and 81 buildings, mostly along Main Street from Fourth Street to Ninth Street, are in a designated National Historic District. "It's the longest historic Main Street in Colorado," city administrator Ryan Stevens said. For years the westernmost blocks, from First to Fourth, were the frayed edge of that street. They were rebuilt through last summer, and the finished product is what you are walking on now.

The businesses that spent 2025 stranded behind orange barricades are the ones worth checking on this month:

• Boudreauxs BBQ — Second-year operation with Chester Schmidt in the kitchen. Was one of the hardest-hit addresses during construction.
• DiRito's Italian — Ran on winter hours through midsummer 2025 because tourists couldn't get to the door.
• Driftwood and Clay Makers Market and Plant Shop — Beki Javernick's store at the First Street end of Main, with work from around fifty local artists on the walls at any given time.
• Yarned and Dangerous — The needle-arts shop that spent last summer routing customers through the back alley.
• McCasland Glass — Held the record last summer for having all three of its entrances blocked at the same time.

The rebuild was expensive and paid for locally. The $2.5 million in improvements at the west end of downtown were paid for with $1.5 million from special city road taxes voters approved in November 2016 (called 2A projects) and a $1 million Main Street revitalization grant from the Colorado Department of Transportation.

There is a longer plan behind it. The blocks feed into the "Main to the Train" effort on Third Street to tie the Royal Gorge Route Railroad depot, the 7-mile-long Arkansas Riverwalk, the whitewater park area and nearby cycling and hiking trails to the downtown area so that people who come to the region for recreation might also visit local businesses. If you have wondered why the wayfinding signs keep changing on Royal Gorge Boulevard, that is the reason. The city is trying to convert highway traffic into foot traffic on the blocks that just got repaved.

The next visible piece of that plan is the Historic Clock Tower lot. Some people wanted the Clock Tower lot to remain a parking area, but 75% of those who attended an open house about the potential design favored a plaza. That parking will be replaced with a paved lot midway down the next block where the city purchased and demolished a condemned former laundry building.

What just opened at 302 Royal Gorge Boulevard

Anchoring the far end of that same downtown grid is a room that did not exist a couple of years ago. Perched above downtown Canon City at 302 Royal Gorge Blvd, Whitewater Rooftop Social delivers elevated eats, craft cocktails, and stunning mountain views from our expansive 2,000 sq ft rooftop patio. Industrial-chic design meets Colorado hospitality in a space built for celebrations, date nights, and everything in between. Watch the sun set behind the Sangre de Cristo mountains as Canon City lights up below.

Two thousand square feet of rooftop is not a small thing in a town this size. It is the first purpose-built sunset venue downtown, and on a weekend evening it is the answer to the question of where to take someone who has just driven in from Denver or Colorado Springs. You are looking west toward the Sangres and down onto the blocks the city just spent five years rebuilding. That is not a coincidence. The rooftop only works because the streetscape underneath it finally does.

The 9th Street reality check

The one place in town where 2026 still looks like 2024 is North 9th Street. If your daily route runs from downtown up toward Cañon Exploratory School or the Family Center Drive area, you already know this. If you have been avoiding it, here is the timeline.

Currently underway are twin projects on two miles of 9th Street, between downtown and the town's northern boundary. On the south end, crews began preparing last fall to replace a water main and then repave the street afterwards. Meanwhile, on the north end, crews are widening the street, adding curbs and sidewalks, and then repaving it. The north end construction has 9th Street closed between Raintree Boulevard and Washington Street, but that work should be finished in another month or so. The south end project currently has 9th Street closed between Floral and Allison avenues, with closures gradually advancing north, and work is expected to be completed this fall.

The final phase of the North 9th Street reconstruction project will be to fully reconstruct the roadway from Mystic Avenue to Meadows Avenue. This project will be posted for bids in the coming days with the intent of awarding a contract to allow construction to begin in January of 2026 and all phases of construction to be complete in September 2026. The roadway reconstruction will also be funded by the 2A tax initiative. Translation for anyone school-shopping or commuting: plan on 9th to be usable end-to-end by football-season Friday nights, not before.

The weekly texture, still intact

Two of the reasons people move to Cañon City in the first place are the reasons the weekly rhythm keeps working even in a summer of half-finished streets and canceled festivals.

The Royal Gorge Route Railroad depot is still boarding trips through the canyon from the west end of downtown, which is exactly the crowd the "Main to the Train" plan was built to catch. The weekly farmers market keeps running. The monthly art walk still routes through the downtown galleries. The Artists Gallery on Main is celebrating its fourteenth year in business in 2026, which in a small downtown is a data point in its own right.

One footnote for late August: the Stage 1 Fire Ban and Stage 1 Water Restrictions currently in effect are worth paying attention to before you plan a backyard gathering or drive up toward Skyline. Check the city's status page the morning of, not the week before.

A late-September plan that still works

If the Abbey lawn was your closing-of-summer ritual, the workable substitute this year is a downtown afternoon that trades one long drive out Highway 50 for a walk on blocks that did not exist in this form last September. Start on the finished west end for lunch, work your way east through Driftwood and Clay for something on the wall you did not expect, and end on the Whitewater rooftop when the light drops behind the Sangres. It is not the same as a Riesling on the lawn under the Abbey cottonwoods. It is what this town is offering right now, and it is more than it was offering a year ago.

Whether you are settling in for the long haul on a street off Main or thinking about what the next chapter looks like on acreage west of town, Western Mountain Real Estate knows this stretch of the Arkansas Valley by name and by block. List With Confidence. Sell With Satisfaction.