Your mission, should you choose to accept it, is to make the most memories possible along Cottonwood’s epic Old Town in just a few short days. Up for it? Then let’s go!
DAY ONE
11:30 a.m.
You’re here! If you left from the Valley, the drive was likely about 90 minutes. Essentially halfway between Prescott and Sedona, Cottonwood’s Old Town, most of which is along Main Street, is not only a wholly walkable wonderland for adults, but the perfect respite from the daily grind. Especially for those who love culinary delights, beer, wine tastings, and outdoor adventure. So, orient yourself in the middle of Main Street, and let’s get started!
12 p.m.
Start your adventure with lunch at Pizzeria Bocce. This modern, indoor-outdoor craft cocktail hotspot and gourmet pizza purveyor is at the northern tip of Main Street. If weather permits, grab a seat around the expansive fire pit or at the ample backyard-style patio to set the chill tone for the trip. Foodwise, you cannot go wrong with the Italian Meat Stuffed Bread, Pesto Chicken Pizza, and Carbonara Pizza. Similarly, the Bocce-rita with blood orange liqueur, Garden Mule with pepper vodka, and Prosecco Sangria with elderflower liqueur are sublime.
2 p.m.
It is time to taste some wine! Pillsbury Wine Company is the perfect start. Helmed by New Zealand-turned Willcox resident Sam Pillsbury (so no relation to the Doughboy), the winery excels at sustainable, estate-grown varietals. Tasting flights, wines by the glass, and full bottles are available during a visit. The Guns and Kisses Shiraz, Wild Child Red Blend, and One Night Stand Rosè are of particular note. While there, ask your server for Cards Against Humanity, which is kept behind the bar for tasters to enjoy along with their wines. From Pillsbury, head across the street to Provisioner Wine’s super intimate indoor tasting space or its larger patio if in a big group. There, grab a bottle of either the Provisoner Red or White before heading a few doors down to sister brand, AZ Stronghold. There, you can pair one of many flights offered with grilled skewers and tapas and even play a game of Connect Four.
6 p.m.
Before it gets too late, take a break from the fun to check into your hotel room. Where should you book? That’s easy: Tavern Hotel. Once upon a time – in the 1920s to be exact – the building was actually the town grocery store. Today, it is less about staples and more about five-star accommodations. Thoughtfully and cheerfully designed – complete with vibrant yellow Adirondack chairs on each balcony – the hotel features 41 standard rooms with hardwood floors, stone-tiled bathrooms with walk-in showers, granite counter tops, vessel sinks, 50-inch flat screen televisions, plush bedding, and spa-quality hair and body products. And while the standard rooms are amazing, the hotel’s cottages and penthouses are the hottest tickets in town, especially the ultra-dog-friendly Tavern Dog House and the Tavern Penthouse. At 2,300-square-feet and with a 180-degree panoramic view of downtown, the Tavern Penthouse is a three-bedroom, two-and-a-half bathroom slice of heaven. When you check in, you will get postcards good for a discount at Crema Craft Kitchen. Be sure to save it as you will need it tomorrow.
7:30 p.m.
For dinner and one final wine tasting, head across the street from the hotel to enjoy the melt-in-your-mouth Gnocchi and the prickly pear-infused, beet dusted Mac & Cheese from chef Christopher “Smithers” Smith at Merkin Vineyards Tasting Room & Osteria. Chef Smith is a Flagstaff native who honed his skills at Robert’s Creekside Café & Grill, Red’s, and Los Abrigados Resort in Sedona. He and his team have greenhouses, gardens, orchards, and olive trees across Arizona, so they can grow as many of their own ingredients as possible. Whatever they can’t grow, they source almost entirely from Arizona farmers and artisans.
DAY TWO
10:30 a.m.
Sleep in, then saunter over to Crema Craft Kitchen and grab a table on the patio lined with colorful umbrellas. There you will see a commercial shipping container painted bright orange and re-imagined as a playful bar in the back! Cool, right? And it isn’t just for show as the cocktails Crema has, even at brunch, will rock your world. Expert tip: Don’t sleep on the specialty mimosas. The food matches the cocktails in flavor and quality, notably the Breakfast Pot Pie, Breakfast Tacos, Bread Pudding French Toast, and Red Chile Glazed Bacon (order some for the table). On the way out, be sure to grab some fresh pastries and other savory nibbles at their bakery for breakfast on your final day as well. And don’t forget to use your discount postcards!
12:30 p.m.
Who is ready to switch gears for a little beer? First, walk over to Belfry Wood-Fired Grill. It is a working brewery with its own outdoor beer garden as well as taproom, offering at least eight of its own beers at any given time (as well as a lengthy list of wines). Next, visit State Bar, an indoor-outdoor spot with yard games overlooking Main Street and a full wall of Arizona beers (and a few Arizona wines) on tap. Finally, next door to State Bar is Strada, which opened in May 2021. It is an eclectic extension of Pizzeria Bocce made from eight industrial-sized shipping containers that opens daily at 4 p.m. Steel beams and Edison bulbs up the ambiance, and beyond about a dozen beers from which to choose, the cocktail menu is a gem, dotted with updated twists on classics with locally sourced ingredients. If getting a little peckish, order a few shareable tapas. You can also get food to-go.
5 p.m.
Head back to the Tavern Hotel for either a siesta or to take advantage of their pool complex, which is still like new. Intimate and adorable, the space can either be a sanctuary, or the perfect spot to turn on Amazon Music and create a synchronized swimming routine with friends. (Yes, it is for hotel guests only.)
7:30 p.m.
Dinner time! Dress up a bit and opt for Nic’s Italian Steak & Crab House. It is dark and dreamy inside and has a great “build-your-own” customized surf and turf menu as well as luscious whole lobster, sweet snow crab, and Tuscan-style steak.
DAY THREE
9 a.m.
Let’s burn off a little of that food and drink before hitting the road! Just about 100 yards from Tavern is the Jail Trail River Walk. Named for its proximity to a river-rock building that used to be the Cottonwood jail (and is now a lovely art gallery), this relaxing and mostly shaded hike wanders 1.5 miles along Blowout Creek. The trail traverses a rich riparian habitat, and wildlife is plentiful, especially birds. Be sure to fuel up on the Crema pastries, too!
11:30 a.m.
It is time to go home. Well, almost. On the way out of town, be sure to stop by Gayle’s Chocolates. The family owned business, a Michigan staple since the 1970s, opened in Cottonwood in 2019. It is a real-life Willy Wonka chocolate factory where you can watch the entire chocolate making process through large glass windows. After taking a peek, and ordering a dozen or so chocolates to go, it is time to hop on the road back home. Until next time Cottonwood!
Written By Alison Bailin Batz
Photographed by Luke Irvin