Discover Twenty Things Under $20 in Gloucester MA

October 15, 2018 / Good to Know, History/Maritime, Outdoor Adventures, Things to Do & See

Making the most of your visit to Gloucester doesn’t mean that you have to spend a lot of money. There are so many great things to see and do for all ages and interests that are free or reasonably priced. Here is our list of Twenty Things Under $20 to discover on your next trip to our beautiful city. Be sure to check our calendar of events while you’re here.


Enjoy fall savings with the MBTA weekend faresMBTA Train ticket from Boston to Gloucester ($2.75 – $10.50 one way) 

Getting to Gloucester is easy. Enjoy a scenic train ride by taking the commuter rail from Boston’s North Station or from one of the other stations on the Rockport/Gloucester line. Check for the schedule and pricing information.

Gataway Mavens Malerie Yolen-Cohen, Discover Gloucester

Admission to the Cape Ann Museum ($12 Adults | $10 Cape Ann Residents, Seniors, and Students | Free for Youth 18 and Under

Explore Cape Ann’s art and cultural history from its collections to special exhibits. It is home to the largest groupings of art by native artist, Fitz Henry Lane, as well as works by other notable local painters and sculptors. Enjoy a family-fun exploration for folks of all ages with kids activities in the Museum‘s Activity Center.

Movie Night Special at the Cape Ann Cinema & Stage ($20 – 2 tickets and popcorn)

Sit back and relax in the comfort of cushy couches and chairs for a movie night any night of the week with freshly popped popcorn at the charming and cozy Cape Ann Cinema & Stage. Visit for movie schedule and show times.

Tree Top Yoga Drop-In Class ($15 Adult/ $13 Student)

Drop into Tree Top Yoga for one of their regular yoga classes to unwind, breathe, stretch, and rebalance. Check for their yoga class schedule available for all levels.

Unlimited Bowling Special at Cape Ann Lanes, Discover Gloucester MA

Unlimited Bowling at Cape Ann Lanes
($15 per person)

Whether rain or shine, bowling is always a fun activity for family and friends during a visit to Gloucester. Cape Ann Lanes is offering a special “all-you-can-bowl” every Tuesday and Thursday from 7:00 pm to close.  

Drive the Back Shore (Free)

Enjoy a casual scenic drive along Gloucester’s picturesque backshore. Stop at any point to pause and soak in the beauty of the scenery and local attractions. Take Route 127 to East Main Street and follow along the harbor through East Gloucester passing by Rocky Neck and down the road to Niles Beach. Continue on to Atlantic Road arriving at the backshore and Bass Rocks with sweeping views of the ocean, and the Twin Lights on Thacher Island. Continue on to 127 to head back to Downtown Gloucester or head over to Good Harbor Beach, or head on up to Rockport to continue on the Cape Ann loop. We love to share your photos on our social channels. Be sure to tag us with #discovergloucester so we can share your adventures with fellow visitors.

A Visit to Sawyer Free Library (Free)

During your visit, stop by the Sawyer Free Library to learn more about Gloucester, to use their free internet access, or to find an event or program of interest. Be sure to check out the wide selection of books about or inspired by Gloucester, or written by a local author. Pull up a chair and happy reading!


A Cup of Clam Chowder at The Gloucester House ($7.50)

During or after sightseeing in Gloucester, warm up at The Gloucester House with a crock of their creamy New England Clam Chowder made with locally caught seafood and bacon.

Virgilio'sFamous Saint Joseph Sandwich at Virgilio’s Bakery ($5.75)

Viva! Delight your appetite with Virgilio’s Bakery famous Saint Joseph’s sandwich served on a delicious freshly baked Saint Joseph roll. Note to self: the bread makes the sandwich!

A Beer Flight at Cape Ann Brewing Company ($12.50)Cape Ann Brewing beer flight, Discover Gloucester MA

Craft beer lovers can enjoy a 4-ounce sampling of six Cape Ann Brewing beers currently on tap of your choosing. Sit inside at one of the long beer hall tables or outside on the waterfront deck to take in the flavor of the atmosphere and beer.

Lobster Roll at Seaport Grille, Discover Gloucester MALobster Roll at Seafood Grille on Thursdays ($12.95)

Craving lobster this season? Enjoy a Seaport Grille award-winning lobster roll with fresh lobster salad served on a New England buttered roll every Thursday throughout the year while dining in style overlooking Gloucester’s waterfront.

Fish Tacos at Jalapenos Mexican Restaurant ($14.95)

Spice up your lunch or dinner at Jalapenos with their delicious Fish Tacos dish. Tempt your tummy with three tacos featuring fresh, local haddock fried in an egg and corn flour batter, served on your choice of corn or flour tortilla, shredded lettuces, pico de gallo, and a side of mango salsa. This dish can be made Gluten Free.


Cupcakes from Cake Ann Cakes , Discover Gloucester MAHalf-dozen Fresh-Baked Cupcakes at Cake Ann Cakes ($20)

Do you have a sweet tooth or need a little something to bring with you to a gathering? Cake Ann Cakes has an amazing selection of freshly baked cupcakes with her famous buttercream frosting. Eat one or eat them all!

Stylish Texting Gloves at Design of Mine ($18)Stylish texting gloves at Design of Mine, Discover Gloucester MA

Keep your hands warm this winter with a pair of stylish texting gloves in a variety of prints available to purchase at the boho-chic boutique, Design of Mine. It’s also a great idea for gift giving.

Handmade Cards at The Brass Monkey ($3.97 – $6)

The Brass Monkey has a wonderful selection of handmade cards by local artists that can be the perfect note to send or keep it for yourself as a treasured piece of art and souvenir from your trip.

Turtle Alley Chocolates, Discover Gloucester MAChocolates at Turtle Alley ($13.00 per half)

Live a little by treating yourself to something decadent with a half-pound of Turtle Alley Chocolates’s famous handmade turtles! Each piece is made with clever little chunks of nuts, buttery caramel, and Hallie’s best chocolate. It’s a sweet treat to give as a gift.

goodlinens studio Discover Gloucester MAA Perfect Gift – Good Linens Studio ($16)

Looking for a gift or a souvenir from Gloucester? Why not something for the bath? Visit goodlinens studio and pick your favorite pattern from one of their beautiful 100% linen, 2-ply striped washcloth and one of the handmade soaps with essential oils ($6). It’s the perfect gift for a friend, family, or for yourself.

Cape Ann Olive Oil, Discover Gloucester MAOlive Oil at Cape Ann Olive Oil ($18)

How much do love cooking with olive oil? Treat yourself to a 375 ml bottle of fresh olive oil from Cape Ann Olive Oil. Select from a wide range of oils and specialty oils to cook or serve with your next special meal. It’s also a great gift idea for the gourmands in your life.

Second Glance Thrift Shop

Almost Anything at Second Glance Thrift Store ($1 – $20)

Enjoy a shopping spree at Second Glance Thrift store where you may find some unique treasures and some really good bargains for $20 and under. Did you know that with every item you purchase, you’re helping Gloucester’s community? Proceeds from all sales support The Open Door’s local relief programs for our community families.

20 Items at The Dollar Store ($20)

From paper goods to party goods, to cleaning supplies, to snacks, most if not all items cost just $1. Load up your basket with 20 dollars worth of items and great savings from The Dollar Store.