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The 8 Retro Road Trip Wonders of Massachusetts

by Eric Hurwitz. Article created March 23, 2017. All photos by Eric unless otherwise noted.

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Driving through Massachusetts and finding old-fashioned department and clothing stores, five and dimes, diners, drive-ins and country stores suggests that maybe places like these got it right the first time -- that is, the vintage retro mom and pop businesses almost always have more authenticity than the big box businesses and chains.

Visiting these small businesses brings about a wonderful feeling, and the owners generally make the experiences even that much better by genuinely connecting with the customer. Check out the old-fashioned Massachusetts destinations below to warm your heart, knowing businesses that have a timeless element
can often bring us back to a time and place that we loved -- or could learn to appreciate, if from a younger generation.

1. Casey's Diner, Natick
Casey's Diner, Natick Massachusetts

First established in 1890 in a four-stool, horse drawn wagon serving hot dogs, Casey's Diner transformed in 1922 as a Worcester Lunch Car Company diner and has been located in Natick since 1927. Some say Casey's is the oldest continuously running diner in the United States! It is, to no surprise, also listed on the National Register of Historic Places. Casey's might just be one of the smallest diners in Massachusetts with barely enough room to walk around, given the tiny structure and crowds. Find a stool at the counter under the double-barreled ceiling and go with the hot dogs that “snap” when first bitten, a delicious cinnamon swirl French toast, double burger for just $6 (at this writing), or a mouthwatering custard pie. Casey's Diner is located at 356 South St., Natick.

  Cheeseburger from Casey's Diner, Natick MA
Cheeseburger from Casey's Diner.

2. Wilson's Department Store, Greenfield Wilson's Department Store, Greenfield Massachusetts

Wilson’s Department Store stands as one of the last independent, family-owned department stores in the United States. The owners live in Greenfield and carry tremendous pride of ownership that respects and honors its 134 years in business at this classic Main Street USA location. The three floors — over 45,000 square feet — offer just about everything you need. I get goosebumps visiting here with the unmistakable but still unidentifiable, delightful old department store aroma, the ancient wooden staircases and old-time elevator giving access to the top floors, the housewares section with its creaky floors and low ceiling, and employees that have that special warmth and hospitality that we sadly see more of in old black and white Hollywood movies than in our current, fast-paced, often impersonal society. Walk into Wilson’s, and it’s like going back in time and being sheltered from the harsh elements of the 21st century. I would travel 90 miles to shop here for Christmas – or any other time of the year, for that matter — than drive three miles to shop at some generic big box store. They have virtually everything for women, men and children: women’s accessories, women’s sportswear, women’s coats, dresses, intimate apparel, juniors, alternative sportswear for women, men’s clothing (including young men and kids) formal wear, shoes, cosmetics, jewelry, luggage, domestics, gifts, clocks, lampshades, housewares, toys, stationery and a great candy counter. This isn’t cheaply made merchandise, either; Wilson’s sells many name brands that sometimes can’t even be found at big box chains. They always have tremendous deals going on. Wilson’s Department Store is located at 258 Main St., Greenfield MA. Tel. (413) 774-4326. Web site: http://wilsonsdepartmentstore.com/.

3. Welfleet Drive-in, Welfleet
Welfleet Drive-in, Welfleet Massachusetts
Photo source: Massachusetts Office of Travel and Tourism Flickr page at https://www.flickr.com/photos/masstravel/15364385547/sizes/l

As the only remaining drive-in on Cape Cod and one of only a handful left in New England, the Welfleet Drive-in offers first-run double features every night in the summer. The Welfleet Drive-In dates back to 1957, but don't let the old-time origins
trick you into thinking this is just another old-time drive-in hanging on to dear life. Quite the contrary with its 100 x 44′screen, FM stereo sound system equipped with Dolby Digital sound, Barco Digital Projection, as well as a playground and snack bar, too. The Welfleet Drive-in open from late May through mid September, and is located at 51 State Highway, Route 6 in Welfleet. Tel. (508) 349-7176. Web site: http://www.wellfleetcinemas.com/drive-in-theatre

4. Balich 5&10, Arlington
Balich 5&10, Arlington MA
Balich 5 &10 photo credit: Balich 5&10 Facebook page at https://www.facebook.com/Balich-5-10-105880669452367/.

Growing up in Arlington as a kid in the 70s, I remember Balich 5&10 very well, but thought even back then that it would become a thing of the past because of the growing number of chain stores in the area taking away so much business from the mom and pop stores. I was wrong, thank goodness! Balich 5&10, dating back to 1954, still thrives with the same business owner and a retail layout virtually unchanged from back in the day.  One of the last five and dime stores in Massachusetts, the Balich 5&10 -- like all great stores of this kind -- is able to jam pack so much merchandise into a relatively small storefront. They still have the deft ability to sell things that we actually need, too, including "crafts, souvenirs, health aids, gifts, stationery, party goods, candy, greeting cards, housewares, notions, toys, glassware, hosiery, yarn, and much more," as stated on its Facebook page. Balich 5&10 is located at 1314 Massachusetts Ave. in Arlington. Tel. (781) 648-3707. Web site: www.facebook.com/Balich-5-10-105880669452367/

5. Furlong's Candies, Norwood
Furlong's Candies, Norwood MA

Furlong's Candies has a sweet business success story: this multi-generation family-run candy house dates back to 1937 and remains incredibly popular by simply not having changed much at all.  Stepping into the old-fashioned candy house takes you away instantly from fast-paced, commuter-crazy Route 1. It's like being sheltered from a harsh world with all the homemade chocolates, fudge, mints, candies, nuts, ice cream and gifts -- as well as polite, friendly, knowledgable service, the kitchsy 1970s-style wallpaper, and that wonderful sweet aroma every step of the way -- to make the experience so pleasant. Many businesses have come and gone on Route 1 in Norwood through the years and it is a testament to Furlong's that they have remained a thriving business, to this very day.  Furlong's Candies is located at 1355 Providence Highway, Norwood. Tel.  781-762-4124. Web site: http://www.furlongscandies.com/

Homemade chocolates from Furlong's Candies in Norwood MA
Homemade chocolates from Furlong's Candies in Norwood.

6. Maynard Outdoor Store, Maynard
Maynard Outddor Store, Maynard Massachusetts
Maynard Outdoor Store photo credit: Maynard Outdoor Store Facebook page at https://www.facebook.com/maynardoutdoorstore/.

There's something heartwarming about a locally-owned store surviving in a world of shopping malls, outlet stores and one-stop shopping superstores. Such is the case with the Maynard Outdoor Store in Maynard, which has been around since 1950. The Maynard Outdoor Store might be the last of a dying breed of locally-run independent clothing stores, but ultimately it's full of life. An exemplary model of how local business should be run, the emphasis is on sales and service. You know the minute you walk in the store that you'll be treated well by staff employed here many years, as well as the newer employees. There are no bad attitudes, trendy, vacuous employees and most importantly, no shoddy merchandise. Faithful clientèle from Maynard and surrounding towns come to the second generation-owned old-fashioned place to buy clothing, shoes, sneakers, jackets for all seasons, hiking boots, baseball gloves, winter gear and the like. The red and white tile floors and original tin ceilings add to the charm. In the back, there is a stretch of red patterned linoleum that every kitchen seemed to have in the 1970s. It's an interesting juxtaposition to the modern world of Nike, New Balance and Timberland shoes. Densely populated rows of clothing on racks and in shelves offer great selections and discounts. There's a wall of jeans that stretches virtually the entire length of the store, and outside there is a markdown rack right next to a hockey net. In the front window are displays, exactly the way business presented itself in this charming building in the early 1900s. Everywhere you look, it's just a beautiful retail place to be -- the way they used to make 'em. The Maynard Outdoor Store is located at 24 Nason St., Maynard. Tel (978) 897-2133. Web Site: http://www.maynardoutdoor.net/.

7. Grafton Country Store, Grafton
Grafton Country Store, Grafton MA
Looking like something out of a small Vermont town, the Grafton Country Store is located only 10 minutes from Worcester -- the second most populated city in New England. Owned by Grafton natives Craig and Carol Dauphinais -- who live right up the street -- the Grafton Country Store offers a wonderful trip back in time with its old-time country store feel and its location in the heart of the Grafton Common Historic District (check out the beautiful town green on the cover and in my book entitled Massachusetts Town Greens). The Grafton Country Store offers a nice selection of home decor, accessory and gift items made in the USA, and has a delightful added bonus: a quaint, relaxing sunny cafe overlooking the historic Grafton town common and offering ice cream, scones, muffins, cakes, tea, coffee, hot chocolate, and smoothies. The Grafton Country Store is located at 2 Grafton Common in Grafton. Tel. (508) 839-4898. Web site: http://www.graftoncountrystore.net.

8. Star Drive-In, Taunton
Star Drive-In, Taunton, Massachusetts
Lobster cakes from Star Drive-In, Taunton MAThe Star Drive-in fulfills critical elements needed for a great, informal retro dining spot: an authentic nostalgic-looking exterior and interior, and an extensive selection of comfort foods, as well as milkshakes and ice cream. Offering fast food made with love rather than heartless corporate standardization, the Star Drive-In does a great job with traditional favorites like burgers, hot dogs, fish and chips, clam strips, clam and lobster cakes (pictured left), and New England clam chowder. What's more, the people working here are so nice, helping make the overall, drive-in like dining experience feel like something out of Happy Days. With a new owner, an absence of the former frozen food served here, a local seafood supplier, and a revitalization to its innately good, old-fashioned looks, it appears that the Star Drive-In has an eye on the future while wonderfully holding on to its dear past that dates back to 1964. The Star Drive-In is located at 205 Myricks St. East Taunton. Tel. (508) 822-7827. Facebook fan page: https://www.facebook.com/205MyricksETaunton/


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