Old Town Scottsdale

Old Town Scottsdale is the Valley's most walkable district and the place most visitors end up most evenings. Packed into about one square mile, it layers several personalities. The historic core around Main Street and Brown Avenue keeps the "West's Most Western Town" look, with covered boardwalks, saddle and boot shops and historic buildings dating back to the town's early years, including the Old Adobe Mission. The Main Street Arts District and Marshall Way are lined with galleries selling Western, Native and contemporary art, and the long-running Scottsdale ArtWalk opens them up on Thursday evenings with artists, wine and music. Fifth Avenue mixes boutiques, jewelry shops and Southwestern souvenirs. To the north, the Scottsdale Waterfront runs along the Arizona Canal with public art, a pedestrian bridge and patios, and just beyond sits Scottsdale Fashion Square, billed as the Southwest's largest luxury retail destination. Museums anchor the day: Western Spirit, Scottsdale's Museum of the West, tells the story of the American West through art and artifacts, and the Scottsdale Museum of Contemporary Art occupies a converted cinema. In the evening the district turns into the Valley's liveliest dining and nightlife scene, with everything from steakhouses and taquerias to rooftop bars and the club-heavy Entertainment District, which gets loud on weekends. In November, Canal Convergence brings ten nights of free large-scale light art, performances and workshops to the waterfront; in 2026 it runs from November 6 to 15 with a Western Nature theme.

Old Town works best as a base or a half-day wander rather than a checklist. Start in the morning at Western Spirit for context, browse the Main Street galleries (many open late morning), and break for lunch on a patio. Afternoons are good for Fifth Avenue shopping and the canal walk, and evenings are for dinner and a drink. Thursday nights are the sweet spot, with ArtWalk turning the arts district into a relaxed street party. A free trolley circulates through Old Town and nearby areas, and parking garages are plentiful and generally free, which makes it easy to come and go from a resort elsewhere.

Know what you are getting into on weekend nights. The Entertainment District around Saddlebag Trail and nearby streets is a club and bar scene that attracts bachelor and bachelorette parties and large crowds, especially during spring training and the Phoenix Open. If you want a calmer evening, stay in the gallery district or along the waterfront, or book dinner at one of the hotel restaurants on the district's edges. Families do well in the daytime, with the museums, the canal, the shops and an ice cream stop; by late evening the mood is adult.

Seasonal events shape the district. Beyond Canal Convergence in November, the cool season brings outdoor festivals, the arts calendar is at its busiest in winter and spring, and the Parada del Sol and Western Week traditions celebrate the town's frontier roots. The district is also close to several of Scottsdale's best hotels, including the midcentury Hotel Valley Ho on its western edge. For a first visit, Old Town is the right place to spend at least one evening even if you stay elsewhere: it is the Valley at its most sociable.