Order Your Dog ‘Up’ at Coney Island

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A simple lunch counter on Southbridge Street was born in 1918 and has blossomed into an iconic staple for the city of Worcester, 100 years hence. Catherine and George Tsagarelis took the reigns in 1938 and coined the name George’s Coney Island, featuring hot dogs for the fair price of a nickel. George raised Coney Island’s neon signage himself, while his wife Catherine made a lasting impression on the neighborhood with her unwavering kindness and penchant for hard work. George and Catherine’s granddaughter, Kathryn Tsandikos has worked to make George’s Coney Island appear visibly frozen in time in the modern age. +discover

Go Diner Hopping

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A fast food boom during the 1960’s led many diners to close throughout the country, but not in Worcester. Many local diners were produced in the city at the Worcester Lunch Car Company, resulting in a loyal customer base. Ralph’s Chadwick Square Diner (Car #660) was manufactured by WLC in 1930 and still serves as a popular destination for live music, burgers, and chili. Miss Worcester (#812) arrived below the elevated tracks of the Providence & Worcester Railroad in 1948, located directly across from the factory where it was constructed, and continues to open on weekdays at 5 a.m. (and weekends at 6 a.m.) for breakfast. Boulevard Diner (#730) serves comfort food 24 hours a day, 7 days a week and even received praise for its persistence from The New York Times. +discover

Ponder the Question of the Day at Helen’s Bakery

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Helen’s Bakery Shop on Greenwood Street has been a Worcester institution for 100 years. The ‘Question of the Day’ begs your input as you wait in line. The robin’s egg blue booths offer a perfect spot to enjoy your treats, as does the old timey lunch counter. A half dozen donuts will cost you less than $5, though we suggest you share them with worthy friends and family. Helen’s also has cookies for every occasion. +discover

Indulge at Gibby’s Ice Cream Stand

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Photo Credit: Brigit C.

Gibson’s Dairy Farm has been serving homemade ice cream to Worcesterites for over 75 years. The Gibson family recipe has likewise been extended to more than 60 flavors including real pistachio, creamy grape nut, and of course, classic vanilla. In addition, Gibson’s still delivers milk in glass bottles throughout the city. +discover

Sip and Screen at Elm Draught House

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Photo Credit: Greg G.

When was the last time you took in a flick at a one-room theatre? One-room means one film, so time your visit wisely. The Elm is ‘cash only,’ but for no less than $10 you will walk away with a ticket, candy, popcorn, and a cold beer. Enjoy the Hollywood sign at the front of the theatre and the vintage movie posters and life size cardboard cutouts of your favorite characters. Along with their regular screening schedule, the Elm hosts private parties and events for large groups. +discover

Take Down Candle Pins at Colonial Bowling Center

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Photo Credit: Alexis H.

Colonial Bowling Center doesn’t possess the sort of 18th-century nostalgia their name might suggest, but it is mind bogglingly transportative to a different era. The pastel glow of Worcester’s candlepin bowling lanes will take you back to the 1960’s, as will the antique cash-only register and handwritten scorecards. A game, some shoes, and a vending machine ice cream will cost less than $10 for you and your friends. +discover

Catch a Show at Worcester County Light Opera

Worcester’s oldest active theater company opened in 1937 and continues its tradition of an annual theatrical season, including a Broadway-style musical. Productions still take place at the Grandview Playhouse as do summer workshops for children. +discover

Round Up a Carload for a Trip to the Leicester Triple Drive-In

The Leicester Triple Drive-In opens every May through August for dusk showings of the top films. Admission for a car load of people is $28, a far cry from large cinema prices. For over 50 years, the Leicester Triple Drive-In has prided itself on providing wholesome family entertainment. On its opening night in 1967, the drive-in showed Elvis Presley’s “Double Trouble” for more than 800 automobiles. Don’t forget to bring a lawn chair, bug spray, and a blanket. +discover

Find Your Half-Loaf Haven at Regatta Deli

Regatta has had a cult grinder following since 1981, courtesy of the signature Regatta Italian served on a half-loaf of fresh Italian bread for just $5. The Prizio family is dedicated to making all customers feel welcome, as evidenced by an abundance of accolades over the years. +discover