Baily's Old Town Temecula

By the 1969 Caddy team · Updated November 8, 2026

If you want to understand how Old Town Temecula became the lively district it is today, Baily’s is part of the answer. The restaurant and entertainment venue moved to Old Town in 2004 and describes itself as a pioneer of the area’s nightlife — one of the businesses that helped transform Front Street from a quiet historic strip into a destination for dinner and music.

The story of Baily’s

Baily’s says it has served the Temecula Valley since 1992. The name will be familiar to wine-country visitors: Baily is also one of Temecula’s founding wine families, with Baily Vineyard & Winery dating to 1986. The Old Town location built on that local reputation and helped shape the evening scene that visitors enjoy today.

More than three decades on, Baily’s remains a reliable choice for a full meal followed by music — a combination that is surprisingly rare in a district where many venues focus on one or the other.

Dining at Baily’s

Downstairs, Baily’s serves lunch and dinner seven days a week, with brunch on weekends. The menu is designed to suit a broad range of tastes, which makes it an easy choice for families, mixed groups and anyone who wants a dependable, full-service meal in the heart of Old Town. Weekend brunch is especially popular with visitors spending a full day on Front Street.

Live entertainment

What sets Baily’s apart is its entertainment program. Live performances take place on indoor and outdoor stages on Friday and Saturday evenings and Sunday afternoons, so a dinner reservation can easily become a full night out. The outdoor stage is a particular pleasure on warm Temecula evenings, when the patio fills and the music drifts down Front Street.

Tips for visiting

• Time your visit for a show — Friday and Saturday evenings or Sunday afternoons.
• Book brunch on weekends if you want a guaranteed table.
• Combine with a stroll along Front Street’s shops before or after your meal.
• Check the calendar on the Baily’s website for the current lineup.

Who will love Baily’s

Couples looking for dinner and a show, groups celebrating a birthday, and visitors who want a classic Old Town night out will all enjoy Baily’s. It is also a natural finale to a chauffeured wine-country day: after an afternoon of tastings, your driver drops you on Front Street for dinner and live music, and you never have to worry about the drive back to your hotel.

For visitors with a connection to Temecula wine, there is a pleasing symmetry in pairing Baily’s with a visit to Baily Vineyard & Winery on Pauba Road — a day that follows one of the valley’s founding names from vineyard to Old Town table.

Because entertainment nights draw a crowd, it is worth planning ahead on summer weekends and holiday periods, when Old Town is at its busiest. A chauffeured arrival also means you can skip the hunt for parking and walk straight in.

Planning your visit

Temecula’s dining scene is busiest on Friday and Saturday evenings and during event weekends such as the Rod Run, Barrel Tasting and the holidays, so reserve ahead whenever a restaurant takes bookings. Many Old Town kitchens open their patios on warm evenings, and a table outside on Front Street is one of the best ways to people-watch. If you are pairing dinner with wine country, plan the tastings for the afternoon and dinner after sunset, and let a driver handle the gap between the two. Groups celebrating a birthday, bachelorette or rehearsal dinner should call ahead to ask about large-party seating, set menus and corkage if you are bringing a bottle from a winery visited that day. Parking in Old Town fills quickly on weekend nights, which is one more reason a chauffeured arrival is the relaxed option.

Best time to go

Weekday lunches and early dinners are the easiest times to get a table; Friday and Saturday evenings, holiday weekends and event days in Old Town are the busiest, so reserve ahead when you can.

Make a day of it

A sample Temecula day built around Baily's Old Town Temecula:

1. Late morning — chauffeured pickup at your hotel and a slow cruise up Rancho California Road.
2. Afternoon — two winery tastings with a lunch stop in wine country.
3. Golden hour — drop-off on Old Town Front Street for photos with the car.
4. Evening — Baily's Old Town Temecula, then a ride back to your hotel with the top down.

Baily's Old Town Temecula at a glance

Details from official and Visit Temecula Valley sources, November 2026. Hours, menus, prices and dates change — confirm on the official website before you go.

Getting to Baily's Old Town Temecula in a 1969 Cadillac

Old Town Temecula is compact and walkable, but parking on Front Street fills quickly on weekends and during events. Arriving by chauffeured 1969 Cadillac solves that neatly: your driver drops you at the door, waits or circles back, and collects you when you are ready — and a red convertible on Front Street’s Western boardwalks makes for the most photographed arrival in town.

Chauffeured hire is $325 per hour with a three-hour minimum, booked and protected through DriveShare. Tell us where you want to go and we will build the route — Baily's Old Town Temecula plus a winery or two, a sunset stop and a ride home.

Book the '69 Cadillac on DriveShare

More things to do nearby

• 1909 — restaurants
• Luke's On Front — restaurants
• Gaucho Grill Argentine Steakhouse — restaurants
• East Coffee — cafes & sweets
• Le Coffee Shop — cafes & sweets

All things to do in Temecula → · Month-by-month events calendar → · Temecula wineries →

Frequently asked questions