Macklemore knows what’s up. What’s old is new, and that includes awesome diners and thrift store finds. These are some of the coolest and quirkiest retro establishments across the state. They’re all special in their own way, but they all share a spirit of old-fashioned cool and incredible vintage experiences. Check them out below!
1. Artcliff Diner, Vineyard Haven
Established in 1943, this adorable diner hasn't lost any of its old-school charm. Their portions are big and beautiful, the atmosphere is cozy, and the service is as warm as the pies. Stop by Thursday through Sunday.
2. Mendon Twin Drive-In
Popular in the '50s and '60s, what's more retro than a classic drive-in theater?
3. Rosebud Kitchen & Bar, Somerville
This Davis square diner opened in 1941, but it doesn't feel dated. The old-fashioned red and black interior and classic menu is still intact, but they've done a great job keeping things lively and attracting a younger crowd. Rosebud has weekly events like Milkshake Mondays (a new boozy flavor every Monday!), trivia on Thursdays, and Vinyl Night on Fridays at 9:30 PM. Their pies are INCREDIBLE, if slightly pricey, and the atmosphere is the perfect mix of retro and fresh.
4. Wellfleet Drive In Theatre, Wellfleet
This place is an awesome retro venue for catching the latest films (and occasionally some classics) but what makes the Wellfleet drive-in really special is how many different activities and events they offer. They host a summer flea market that is gigantic and well-known for its selection of unique wares. There's a small playground for the younger movie-goers to tucker themselves out on before settling down for the movie. Last but not least, play a round of retro mini golf on their vintage 18-hole course.
5. Whatley Diner, Whatley
With jukeboxes at each booth and tasty homemade meatloaf (heck, pretty much tasty homemade everything) this place is a no-frills, family friendly, old-fashioned diner. Definitely the kind of place you can imagine the server remembering your name.
6. Interskate 91 North, Hadley
Located on the second floor of the Hampshire Mall, this roller rink is unique in that its skating floor is hourglass-shaped rather than the usual oval. Skate rental is only $4.50 plus tax.
7. Moran Square Diner, Fitchburg
Born in 1940, this diner serves honest food at incredibly low prices. Open at 6 am for breakfast, this is definitely a place that keeps things simple, tasty, and comforting.
8. West Concord Five and Ten, Concord
Lightbulbs? Check. Twelve bouncy balls? Petunia seeds? Bag of bagels? Check, check, and check. Just an old-fashioned everything shop with retro prices to match its retro wares. A local landmark and a beloved purveyor of toys and treats.
9. South Boston Bowlarama
Bowling is retro. There's no two ways about it. If you need a place that lets you bowl like your parents, head on down to South Boston Bowlarama. This place has old-fashioned pencil and paper scoring, wooden ball returns, and retro arcade games. All you need for a great night is an ugly pair of shoes, some dwarfish balls, and those shiny candlepins. And hopefully some friends.
10. Balich 5 & 10, Arlington
More than just a dime store, this place is a local treasure. First opened in 1934, this is one of only a couple true five and dime shops left in Massachusetts. Obviously the prices are cheap and the goods a little quirky (e.g. a window display of rubber chickens), but shopping here is supporting a bit of New England history.
11. Ball Square Bowling, Somerville
This is an old-fashioned little bowling alley featuring eight lanes of candlepin bowling. And you can bring your own food, beer, and wine! The interior feels like it hasn't seen much change since the 60s, but that's just fine by us. When many modern bowling alleys make you feel like you stumbled into a dance club wearing the worst shoes imaginable, this place is simple, clean, and a plain old good time.
12. Boulevard Diner, Worcester
Breakfast sort of steals the show when you're talking about diners, but this place can handle all three daily meals with style. Check out the grapenut custard for a classic Massachusetts dessert or stick with one of their tried and true sandwiches. The pepperburger is worth your time.
Of course we know that we didn’t include ALL the incredible retro spots across the state. Share with your friends and tell us about us your suggestions and favorite local gems in the comments!