Retail Therapy: Six Spectacular Shopping Vacations

When you’ve seen all the museums you can handle, toured all the caves, canyons and vistas, and seen everything from the Statue of Liberty to the Golden Gate Bridge, what’s left for your next vacation destination? Shopping!

When you’re tired of the shopping malls and cookie-cutter retail destinations of your hometown, then it’s time to incorporate a little retail therapy into your next three-day weekend. There is life and shopping beyond the look-alike malls, and a shopping vacation on Fifth Avenue in New York, on the Las Vegas strip, or enjoying the boutique shops in quaint New England destinations like Greenwich, Connecticut will always yield shops you never knew existed. You’d better take an extra suitcase, you’re going to need it when you come back.

Greenwich, Connecticut

Just a 40-minute train ride from Manhattan, Greenwich Avenue – known simply as “The Avenue” to locals – combines the upscale feel of Fifth Avenue, with a quaint, small-town New England vibe. You won’t find a single chain store, but you will find plenty of incredible boutiques and cafes. You will find the Greenwich branch of that shopping heaven called Saks Fifth Avenue, and to make it even better, when you’re done shopping at Saks, go right next door to a legend called Something Natural, a local favorite with wonderfully large sandwiches made on their house-baked Portuguese bread. It’s the perfect place to enjoy lunch (and one of their wonderful chocolate chip cookies) while you plan your next shopping target.

One of the best known of all the fabulous Greenwich Avenue Stores is Richards of Greenwich, a trendy department store where you can find all the best designers in both men’s and women’s apparel – and personalized service that is hard to come by these days. Also be sure to stop by Splurge on Lewis Street to pick up a few gifts to take home, and Out of the Box for well, clothing and accessories that are out-of-the-box.

A wonderful thing about Greenwich is that while you’re visiting, you’re probably not going to stay in a standard-issue airport motel. More than likely, you’ll want to take advantage of one of the quaint New England bed-and-breakfasts like Stanton House Inn, an Historic mansion and one of the most romantic accommodations in the city.

Tokyo, Japan

You can always tell a serious world traveler by their living rooms. Shopping big on your overseas trip does require a little extra in terms of logistics, and that delightful, oversized bookcase you saw in the Ginza will require careful crating and filling out some confusing customs papers – but it’s all worthwhile when your guests see it in your living room.

Some of the city’s department stores are truly a wonder in themselves, and a shopping trip in Tokyo is more than just shopping – it’s an experience. And it usually involves really good food. Department stores often have food halls in their basements called “depachika”, which are wonderful places to take a quick break from shopping. You can get just about anything there, and you’ll often see local delicacies and plenty of beautifully wrapped items to take home as gifts.

Department stores in Tokyo are nothing like the cookie-cutter shops of the West, and you’ll often find special exhibitions in a department store’s craft floor. Unlike in the United States, where artists dream of exhibiting at a top gallery, in Japan, the goal is to get into an exhibition in a department store’s craft floor. Be sure to stop off at the kimono floor at Mitsukoshi – even if you’re not planning on buying one of these exquisite garments, it’s worth seeing and exploring.

Manchester, Vermont

Nestled in the scenic Green Mountains, Manchester, Vermont, is a small town with a big shopping experience that will satisfy the most advance shopper around! It has an impressive mix of locally owned boutiques, designer outlets, and home to Orvis’s flagship store. Founded in 1856, the Orvis Company makes the trip to Manchester worthwhile. The company is now the oldest mail-order catalog company in the United States. The Manchester store offers much more than a shopping experience. After you’ve shopped and bought all your outdoor gear for your next adventure, you can stick around for a free fly-fishing class, and even visit the American Fly Fishing museum next door.

Manchester is very well known for its tradition of handmade, quality products, and is in the top five states with the most working artists per capita. Pay a visit to Epoch, a cooperative gallery staffed by 18 local artisan members, to pick up some one-of-a-kind artwork to bring back home and decorate your living room. The shop features paintings, pottery, fine woodwork, and jewelry – and the best part of shopping at Epoch is that the artists are on hand to share their unique view of the creative process, helping you find that perfect one of a kind piece.

Chicago, Illinois

Who needs the coast? Some of the best shopping – and plenty of world-class restaurants – are available right in the heart of the country in Chicago. The place to start is the Magnificent Mile, a famous stretch of Michigan Avenue just north of the Chicago River. One of the most visited shopping districts in the United States, the Magnificent Mile is dotted with a number of current and soon to be flagship stores from some of America’s most iconic brands including Apple and Starbucks. There is even a 750,000 square foot mall located in a 74-story building on the Mag Mile! If you don’t know where to start, Free Chicago Walking Tours has a tour dedicated to this shopping district.

But there is also a distinct “neighborhood vibe” to some of Chicago’s shopping as well, so don’t forget to visit the surrounding neighborhoods and streets such as Wicker Park and Lincoln Park. In Wicker Park you will find countless independently owned and operated boutiques along Milwaukee Avenue between Division and North Avenue and on Division Street between Milwaukee & Damen. There are enough bars and restaurants along these streets to ensure you can keep going all day too.

Similarly in Lincoln Park there is the Armitage-Halsted Historical District that introduced Chicago to mixed-use buildings in the late 1870s. Many of these same structures and architecture still exists today, with the tenants occupying the retail space on the ground level offering cutting edge cosmetics, the latest fashion and even an opportunity to create your own fragrance. And from here you’re steps away from Oz Park, named after the author of The Wonderful Wizard of Oz and a few more blocks away from Lincoln Park.

Frederick, Maryland

It is not quite as well-known as the larger shopping venues, but this historic down is a must-see for anyone vacationing in the greater DC area. Downtown Frederick features over 200 locally owned boutique shops offering everything from clothing, to pottery, to hiking gear. As you shop you’ll notice that live music is everywhere you turn. If you visit on First Saturday (the first Saturday of every month) you will also find street vendors, shops open late into the evening, and special events inside each shop like wine tasting, games, and special deals. This Historic Main Street is the perfect mix of quaint small-town charm, historic architecture, impressive public art scene, and modern day amenities. Historic buildings housing art galleries, cultural venues and restaurants are also plentiful, meaning there is no need to leave the area if you need a shopping break. You can park the car in one of five inexpensive garages and leave it all day.

Besides one of the region’s premier arts and entertainment districts, Downtown Frederick is unquestionably the region’s most significant restaurant district for local, signature eateries including television’s Top Chef contestant Bryan Voltaggio’s nationally acclaimed restaurant, Volt. Visitors looking for low key unique eats will love Pretzel Pizza Creations, where everything is made using pretzel dough or The North Market Pop Shop, which offers over 400 kinds of vintage soda that can be paired with locally made ice cream for a float you can’t find anywhere else. Residential spaces above and around many businesses give Market Street a certain hometown feel. Many locals walk or bike everywhere, visitors may see familiar faces throughout their stay. Bowls of water for pets are found outside of many shops and restaurants, welcoming dogs to join the fun and even come inside many of the shops. Local festivals like “In The Street” draw a huge crowd of both locals and visitors to this nationally designated Main Street community each year. Guided walking tours and candlelight ghost tours around Frederick’s beautifully revitalized, 50-block downtown area show off sites linked to celebrated “locals” like Francis Scott Key and Civil War heroine Barbara Fritchie. Market Street also connects to Carroll Creek Park, a linear park similar to River Walk.

Oxford, Mississippi

About an hour outside of Memphis, Oxford, Mississippi is the heart of southern charm – and the best shopping the south has to offer. The city has a rich literary history, so before you set out on your shopping journey, take time to visit Rowan Oak, the estate of author William Faulkner, and stop in at Square Books, voted “Bookstore of the Year” in 2013 by Publisher’s Weekly — the perfect resting place for exploring literary works, many written by authors who call Oxford home.

Flanking the Square, which was incorporated in 1837, you’ll find delightful boutiques, independent bookstores, art galleries and eateries. A historical point of interest, Neilson’s–founded in 1839, is the oldest department store in the South. A few must-see stops include the Stash by the Weathervane home store. Try Jones at Home Interiors, opened in February 2014 by mother and son Christy and Charles Jones, for classic, contemporary solutions that make a house a home.

Antique stores abound in Oxford, as do options for customized gifts – making the town a go-to destination when it comes to finding something for everyone on your list. But shopping is by no means the only thing to do in this fascinating and culturally-rich city, and while shopping the Square, don’t miss the Mississippi Blues Trail marker, which commemorates many of Oxford’s musicians and the blues heritage that exists in the Mississippi Hills.


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