Photo: Sprinkles Cupcakes (Chicago)/Facebook

The 5 Best Dessert Walking Tours in the US

United States Insider Guides
by Eben Diskin Sep 19, 2019

Restaurants might grab most of your attention when you show up in a new city, but everyone knows that dessert is more important than dinner. There’s always room for dessert, even if you’ve indulged in a hearty meal with appetizers and a hefty entree. The main obstacle is deciding which place to go. Cafes tend to blend together. Pastry shops may appear on every corner, but you don’t want to waste your sweet tooth on a less-than-stellar treat. That’s where dessert tours come to the rescue. Designed to totally eliminate FOMO, these tours will bring you to the best sweet shops in town and let you try a bit of everything. Here are a few of the best dessert walks in the US.

1. Cupcakes and Ice Cream Walk in Chicago

Chicago’s Magnificent Mile might be named for its abundance of luxury hotels, shops, and trendy restaurants, but cupcakes are a strong addition. This famous street is home to some of Chicago’s most delicious cupcake spots, and on the Cupcakes & Ice Cream Walk, you’ll get to see (and taste) them all. Among many others, some of the best-known stops include Chicago staples like Sprinkles and Molly’s. And once you’ve filled up on cupcakes, you can indulge in second dessert with a healthy helping of ice cream available at multiple stops. To keep the memory alive long after the walk is over, buy take-home treats at Sacred Grounds Bakery along the way.

Tickets to the Cupcakes & Ice Cream Walk are $50 each and can be purchased online. Tours run every Saturday and Sunday from 1:00 PM to 2:30 PM. The American Walks company offers a variety of other food and dessert-themed walks in Chicago, like the Donuts & Sweets Walk.

Cost: $50, purchased online

2. Chocolate Tour in Newburyport, Massachusetts

Newburyport, Massachusetts, might seem like a classic New England seacoast town, but when you look under the hood, this town holds a few surprises. One of them is the annual NBPT Chocolate Tour, which is the perfect way to explore this small historic town. Taking place in mid-May, this chocolate tour will take you around Newburyport’s downtown area, which is defined by its cobblestone sidewalks and squares, riverside boardwalk, and seafood restaurants. It’s not a guided tour but rather allows you to explore the town at your own leisure and hit as many of the stops as you like. Yes, you can visit the same place more than once.

The tour includes 30 Newburyport stores — which, given the town’s small size, is pretty much all of them — doling out handmade caramels, chocolate cake, ice cream, chocolate-covered strawberries, and more. A chocolate fountain has even been known to make the occasional appearance.

Cost: $20, purchased at the Unitarian Church on Pleasant Street

3. Hell’s Kitchen Dessert Tour in New York City

Photo: Sugartooth Tours/Facebook

Hell’s Kitchen is known for its many restaurants, and this neighborhood in Manhattan is also home to one of the country’s best dessert walks. Sugartooth tours will not only expose you to tons of samples but also give you some delicious insight into the area’s history. Sweets include artisan handcrafted chocolates, traditional American pies, homemade fudge, frozen custard, and some of the best cookies and Greek pastries you can find in New York City.

The tour accommodates between three and 16 guests, and it begins in Times Square before heading into Hell’s Kitchen. It then progresses to 9th Avenue, where you will also learn about this street’s culinary history.

Private tours are available for groups of six or more, and they can even be personalized to suit your group’s specific taste and needs. Tours run most Saturdays at 1:00 PM though private tours can be requested for other times.

Cost: $55, purchased online

4. Chocolate Tour of Back Bay in Boston

Boston might be known for its place in American history, but the city’s chocolate history is just as tantalizing. On this chocolate tour of Boston’s Back Bay, you’ll learn all about the history of chocolate as it relates to Boston, all while tasting tons of treats. Each guest will have the opportunity to try chocolate candies prepared at the area’s bake shops, including Max Brenner, L.A. Burdick, and Gourmet Boutique. You will also receive a goodie bag with some additional surprises.

Private chocolate tastings and wine pairing classes are also available for those who are so inclined. The group chocolate tour takes around 2.5 hours and leaves every Saturday at 10:15 AM.

Cost: $50, purchased online

5. Gourmet Chocolate Tour in San Francisco

Photo: Gourmet Walks/Facebook

The fanciest chocolate tour on this list takes place in San Francisco. The city is in the midst of a gourmet chocolate boom, where quality beans, exotic fillings, new production methods, and creative packaging are taking the scene by storm. Even if you’re not a chocolate connoisseur yet, you will be by the end of the Gourmet Chocolate Tour. You’ll learn exactly what sets fine chocolate apart and sample a wide range of local San Francisco chocolates, including unshelled truffles, Swiss Champagne truffles, hazelnut Parisian macarons, and decadent chocolate velvet cupcakes. The tour will also educate you on San Francisco’s chocolate history, taking you through the waterfront area where Ghirardelli first established his famous shop during the Gold Rush.

Guests will each receive a Guest Loyalty Card, which means VIP discounts and benefits at seven different chocolate boutiques. The tour takes between 2.5 and three hours and runs from the waterfront to Union Square. The tour begins at 10:30 AM on Mondays, Wednesdays, and Fridays; at 12:00 PM on Tuesdays and Thursdays; and at 2:00 PM on Saturdays.

Cost: $55, purchased online

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