Downtown Riverside is at its most alive during the Festival of Lights. The Mission Inn glows, sidewalks fill with visitors, and parking becomes a competitive sport. Thousands of people come to wander, take photos, and soak in the atmosphere. Far fewer step inside the bars and restaurants that keep downtown running the rest of the year.

This season felt like the right time to slow down, step inside, and actually spend some money locally. The Old Fashioned became the excuse. It’s one of the oldest cocktails still in rotation, simple enough to order anywhere, but revealing enough to tell you exactly what kind of bar you’re sitting in. Over the past few weeks, I moved through downtown tasting Old Fashioneds, not to crown a winner, but to see what happens when you treat the drink as a conversation instead of a transaction.

At The State, the default Old Fashioned is solid and confident, built well enough that it doesn’t demand attention. But ask about an upgrade and the bar shows its hand. Their Eagle Rare 10 Year “State Select” Old Fashioned is where intention becomes obvious. Barrel selection matters here. Barrel-aged maple syrup rested in 12-year Rip Van Winkle barrels and walnut bitters deepen the drink into something slower and more reflective. It’s not sweeter so much as richer, and it rewards sitting with it.

The Lobby takes a lighter, brighter approach. Their standard Old Fashioned uses Old Forester 86 with a bitters balance that brings orange into the body of the drink rather than just the nose. It’s approachable and clean. Talking whiskey with the bartender led to a Rittenhouse Rye version built with the same ratios, and the difference was immediate. The rye tightened the structure, pushed spice forward, and made the drink feel more deliberate. Same recipe, different personality. That contrast only exists if you’re willing to engage.

W. Wolfskill leans unapologetically traditional. Their Old Fashioned is built on Evan Williams Bottled-in-Bond, and it announces itself with a healthy burn that quickly gives way to vanilla and caramel, with oak lingering quietly at the back of the palate. It feels grown up and honest, perfectly matched to the bar’s mid-century modern atmosphere. W. Wolfskill also invites exploration by design. Their menu lists every whiskey with a clear price, and for three dollars more, they’ll turn any of them into a cocktail. Curiosity isn’t treated like a disruption here. It’s built into the system.

Dapper Dine & Lounge sits slightly off the main downtown walkways, and that distance matters. The default Old Fashioned uses Woodford Reserve and delivers exactly what most people expect from the drink: smooth, oak-forward, bitters doing their job, orange peel staying politely in the background. It’s well made, but familiar. At $19, you’re paying less for experimentation and more for ease. Parking is plentiful, the room is calm, and you’re spared the Festival of Lights shuffle. Dapper is a reminder that value isn’t only about what’s in the glass. Sometimes convenience is the upgrade.

The Mission Inn offers a lesson in how intent shapes experience. The Presidential Lounge’s Old Fashioned is serviceable and priced for the setting, aimed at hotel guests passing time between plans. The bartender is friendly and attentive, but the program is clearly designed for speed and safety rather than exploration. Walk a few steps in the opposite direction and the story changes. In the California Lounge, asking the right question leads to Duane’s Old Fashioned, built on Wild Turkey Rye with a caramelized orange simple syrup. It’s richer, warmer, and far more expressive. An upgrade to Basil Hayden softens the edges and shifts the balance again. Same building, same hotel, completely different philosophy. When it comes to the Mission Inn, your instinct will tell you to take a right as you walk in, but you should take a left.

Proabition on Main Street carries the reputation of a whiskey bar, and their Old Fashioned reflects that identity. The current house build uses Elijah Craig with simple syrup and Angostura, sturdy and oak-forward. When offered the smoked option, it’s worth declining. The added smoke over-emphasizes the bourbon’s existing char and flattens the balance. Uns­moked, the drink is cleaner and more confident. Asking about upgrades led not to a whiskey swap, but to a bartender-driven riff built on citrus peels, honey, and a splash of triple sec to compensate for missing orange bitters. It was bright and enjoyable, but also revealing. Some of the most interesting Old Fashioneds aren’t house recipes at all. They’re personal builds that travel with the bartender. Those moments can’t be ordered twice, and that’s part of the appeal.

For those keeping score at home, the price range across downtown tells its own story. The Lobby offers one of the most accessible Old Fashioneds downtown at $12, with a rye upgrade at $13. W. Wolfskill lands in a similar range, with their Evan Williams Bottled-in-Bond Old Fashioned at $13 and a transparent model that adds three dollars to any whiskey you choose. The State’s Eagle Rare 10 Year Select Old Fashioned comes in at $19, reflecting the care put into barrel selection and ingredients. Dapper Dine & Lounge also sits at $19, trading innovation for convenience. At the Mission Inn, the Presidential Lounge’s Old Fashioned runs $19 plus tax, while the California Lounge’s Duane’s Old Fashioned is $18, with a Basil Hayden upgrade at $20. Proabition falls into the same premium downtown tier, with pricing that reflects its whiskey-bar reputation rather than bargain hunting. None of these drinks are inexpensive, but each price point makes more sense when you understand what the bar is prioritizing.

After all these stops, there is no single best Old Fashioned in downtown Riverside. The winner isn’t a bar or a bottle. It’s the person willing to sit down, order the default, ask a question, and let the bartender take it somewhere new.

During the Festival of Lights, downtown becomes a destination. The bars along these streets survive by being more than scenery. They survive when people step inside, engage, and spend their money locally instead of just passing through. The best Old Fashioned is the one that turns a night of wandering into a night of connection, and downtown Riverside has plenty of those waiting.