Travis T.
Yelp
I've lived in Scottsdale a couple times in my life and have always enjoyed visiting the Old Town area. The Thursday night artwalk is one of my favorite things things to do. It's a lot more chill than the other Valley artwalks and has some really nice galleries that showcase incredible high end art. Old Town Scottsdale is nestled within nine walkable neighborhoods and been around since the late 1880's. It's unique because it has a nice blend of Old West charm, Southwestern flair, high-class shopping, bars, art and fine dining. There is something here for all ages.
The art galleries open up for viewing every Thursday night for the artwalk. The Civic Center has a LOVE sculpture, the Museum of Contemporary Art and a Spring Training facility for the S.F. Giants. The Waterfront is a nice place for a stroll after shopping at nearby Scottsdale Fashion Square and hosts the Canal Convergence each year. For hotels, I have done staycations at The Valley Ho for many years. It has a long history in Scottsdale and was built in the 50's. I love the Hawaiian them and many celebrities have stayed there over the years.
If you are going to visit Old Town, The Sugar Bowl is a must. It's an old ice cream parlor that has been a staple in Old Town Scottsdale since 1958. My favorite breakfast spots are the Breakfast Club and JoJo Coffeehouse. Some of my other favorite restaurants over the years have been The Mission, AZ 88, Los Olivos, Old Town Tortilla Factory, Roaring Fork, Café Monarch, Olive and Ivy, Farm and Craft and Grimaldi's.
Even though I don't frequent clubs much these days, Old Town Scottsdale is also known for their club and bar scene. I grew up hanging at a dive bar called the Coach House and still stop in from time to time. The Kaz Bar is a hidden gem that has live music and is a favorite of mine as well.