The Chillavista Guidebook
Food scene
Tonno Restaurant
2 Main StA higher end dining experience
Seaport Grill
6 Rowe SquareClassic New England fare with great views.
Great piano bar with live music and specialty cocktails. Put some bread in the jar.
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Drift
3 Main StGreat piano bar with live music and specialty cocktails. Put some bread in the jar.
Outdoor or indoor dining on the water. Expansive food (even sushi) & drink menu. Catch some live music at the attached venue.
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Minglewood Harborside
25 Rogers StOutdoor or indoor dining on the water. Expansive food (even sushi) & drink menu. Catch some live music at the attached venue.
Great Seafood on the Ocean. Eat outside or inside. Live music on the weekends! Blue Collar is open seasonally but the Gloucester House remains open all year.
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Blue Collar Lobster Co at The Gloucester House Restaurant
63 Rogers StGreat Seafood on the Ocean. Eat outside or inside. Live music on the weekends! Blue Collar is open seasonally but the Gloucester House remains open all year.
Great for any season! Enjoy a cocktail with ocean breezes in the summer and get cozy inside an igloo on the deck in the winter.
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Mile Marker One Restaurant
75 Essex AveGreat for any season! Enjoy a cocktail with ocean breezes in the summer and get cozy inside an igloo on the deck in the winter.
If you love dive bars and have seen the movie "A Perfect Storm" then this is the place for you. You'll find plenty of cold beers and fish stories here.
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Crow's Nest
334 Main StIf you love dive bars and have seen the movie "A Perfect Storm" then this is the place for you. You'll find plenty of cold beers and fish stories here.
Pratty's CAV
10 Parker StFeatured in the movie, CODA...a true Gloucester dive bar.
Fresh bread, the best subs and all things Italian.
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Virgilio's Italian Bakery
29 Main StFresh bread, the best subs and all things Italian.
Located inside the Beauport Hotel. This is a classy spot on the water.
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1606 Restaurant & Bar
55 Commercial StLocated inside the Beauport Hotel. This is a classy spot on the water.
This is a classic New England seafood restaurant. Come as you are. You will have leftovers...the plates are huge!
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Causeway Restaurant
78 Essex AveThis is a classic New England seafood restaurant. Come as you are. You will have leftovers...the plates are huge!
These guys know how to do it. They have unique flavors like Fruity pebbles ice cream and are always changing their menu.
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Holy Cow Ice Cream Cafe
80 Pleasant StThese guys know how to do it. They have unique flavors like Fruity pebbles ice cream and are always changing their menu.
Seasonal spot in Rockport on the Ocean. BYOB and eat some lobsters and fried clams by the ocean. Our favorite time of day is sunset!
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The Lobster Pool
329 Granite StSeasonal spot in Rockport on the Ocean. BYOB and eat some lobsters and fried clams by the ocean. Our favorite time of day is sunset!
Two Sisters Coffee Shop
27 Washington StCute and classic coffee and breakfast spot.
A favorite breakfast spot of locals and tourists alike. About a 2 minute drive from the house. The eggs Benedict is our favorite! They also serve lunch and dinner.
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George's Coffee Shop
178 Washington StA favorite breakfast spot of locals and tourists alike. About a 2 minute drive from the house. The eggs Benedict is our favorite! They also serve lunch and dinner.
Pickup seafood to go. Cook at home or buy prepared. You can’t go wrong either way!
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Turner's Seafood Market & Fish n Chips Shoppe
4 Smith StPickup seafood to go. Cook at home or buy prepared. You can’t go wrong either way!
Short & Main
36 Main StWood fired pizza, pasta and great cocktails
Lobsta Land Restaurant
84 Causeway StThis spot gets packed! A fan favorite.
Oak to Ember
Brand new and upscale restaurant in downtown Gloucester.
Great coffee, tea & breakfast options right downtown.
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Lone Gull Coffee House
146 Main StGreat coffee, tea & breakfast options right downtown.
BISHCO
51 Main StOn the go or sit at a few of their casual tables. Soups, salads, smoothies & sandwiches.
These guys have a HUGE menu!  They are less than a 10 minute drive away but also deliver. Subs, sandwiches, calzones, pizzas, soups, salads, pasta, rice plates and even breakfast sandwiches.
Firing Up Pizza and Grill
These guys have a HUGE menu!  They are less than a 10 minute drive away but also deliver. Subs, sandwiches, calzones, pizzas, soups, salads, pasta, rice plates and even breakfast sandwiches.
An unassuming Japanese inspired restaurant. The staff here is incredibly nice and the food is always hot and fresh. It’s our families go to sushi spot in Gloucester. Spring rolls are a must! Please note: They have a seasonal liquor license.
Midori
An unassuming Japanese inspired restaurant. The staff here is incredibly nice and the food is always hot and fresh. It’s our families go to sushi spot in Gloucester. Spring rolls are a must! Please note: They have a seasonal liquor license.
Mom's Kitchen
Homey breakfast place with food made with lots of love ❤️
Famed chef and James Beard Award–winner, Barbara Lynch’s take on an old classic.
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Rudder Restaurant
73 Rocky Neck AveFamed chef and James Beard Award–winner, Barbara Lynch’s take on an old classic.
Salted Cod Arthouse
Small bites, Wine Bar and art.
Duckworth's Bistrot
197 E Main StHandmade, from scratch pastries, desserts & meals using locally grown fruits, vegetables, flours & dairy products. Tucked away on Duncan @ Main St.
Source Bakery
Handmade, from scratch pastries, desserts & meals using locally grown fruits, vegetables, flours & dairy products. Tucked away on Duncan @ Main St.
Open until midnight during the week and 1am on weekends for a late night option! McDonald’s is close by as well and open until midnight in the drive thru.
Domino's Pizza
Open until midnight during the week and 1am on weekends for a late night option! McDonald’s is close by as well and open until midnight in the drive thru.
Speakeasy sushi inside of a wine and cheese shop. Prepared and served by Sang Lee himself. This is a must book ahead reservation. He only has about 8 seats available and they book out sometimes months in advance…but he does have a waitlist. He typically does his pricing per head and always omakase style. This experience is a real treat!
Sushi Sang Lee
Speakeasy sushi inside of a wine and cheese shop. Prepared and served by Sang Lee himself. This is a must book ahead reservation. He only has about 8 seats available and they book out sometimes months in advance…but he does have a waitlist. He typically does his pricing per head and always omakase style. This experience is a real treat!
We’ve been told they have a separate vegetarian menu so we’ve added this location as a good option for our vegetarian guests!
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Franklin Cafe Cape Ann
118 Main StWe’ve been told they have a separate vegetarian menu so we’ve added this location as a good option for our vegetarian guests!
Gloucester and Beyond
Gloucester is rich in Italian and Portuguese heritage. It is also known for its fishing and Lobster industry which is why you will find great seafood wherever you go. Many a movie has been filmed in Gloucester for not only its idyllic scenery but realism of a real New England fishing town. Gloucester hosts many events, weddings, tournaments and races in town... There is little something for everyone!
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Gloucester
Gloucester is rich in Italian and Portuguese heritage. It is also known for its fishing and Lobster industry which is why you will find great seafood wherever you go. Many a movie has been filmed in Gloucester for not only its idyllic scenery but realism of a real New England fishing town. Gloucester hosts many events, weddings, tournaments and races in town... There is little something for everyone!
Enjoy this quaint town just next door to Gloucester. Bear Skin neck is a popular spot to grab a bite, shop and take in the ocean.
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Rockport
Enjoy this quaint town just next door to Gloucester. Bear Skin neck is a popular spot to grab a bite, shop and take in the ocean.
A quick train or car ride from Gloucester, there is so much to do in Salem! One of the oldest maritime ports in the country, infamous for the Salem Witch Trials and more recently all things spooky & Halloween 🎃
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Salem Maritime National Historic Site
160 Derby StA quick train or car ride from Gloucester, there is so much to do in Salem! One of the oldest maritime ports in the country, infamous for the Salem Witch Trials and more recently all things spooky & Halloween 🎃
Sightseeing
Take a catamaran cruise around the Stellwagen Bank National Marine Sanctuary
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Cape Ann Whale Watch
415 Main StTake a catamaran cruise around the Stellwagen Bank National Marine Sanctuary
Built in 1832 this lighthouse is a local landmark. While here check out the Eastern Point wildlife Sanctuary part of the Massachusetts Audubon.
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Eastern Point Lighthouse
Built in 1832 this lighthouse is a local landmark. While here check out the Eastern Point wildlife Sanctuary part of the Massachusetts Audubon.
Artist Row - Art galleries, storefronts in this funky little neighborhood.
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The Cultural Center at Rocky Neck
6 Wonson StArtist Row - Art galleries, storefronts in this funky little neighborhood.
The Friki Tiki of Gloucester Harbor
73 East Main StreetTake a Tiki boat on a harbor cruise and see the sights.
Active lighthouse built of cast iron & brick in 1881 to guide boats into the town's inner harbor.
Ten Pound Island Lighthouse
Active lighthouse built of cast iron & brick in 1881 to guide boats into the town's inner harbor.
7 Seas Whale Watch
63 Seas WharfPopular Whale watch in Gloucester.
Gloucester Fisherman's Memorial
Visit and take photos at this famed location.
Schooner Ardelle
23 Harbor LoopSail around on Schooner Ardelle
Things to do
Hammond Castle Museum
80 Hesperus AvenueCheck out this beautiful castle on the water.
Cape Ann Museum is a great stop to make while in Gloucester. All of the photos hanging in the hall outside of the 2nd floor kitchen come from their historic archives.
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Cape Ann Museum
27 Pleasant StCape Ann Museum is a great stop to make while in Gloucester. All of the photos hanging in the hall outside of the 2nd floor kitchen come from their historic archives.
Cape Ann Lanes
53 Gloucester AveBowling. Arcade. Brewery.
A 2 minute drive. All new movies. Make a night of it! Have dinner at Causeway, catch a movie and then grab some ice cream next door at White Farms.
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Gloucester Cinema
74 Essex AveA 2 minute drive. All new movies. Make a night of it! Have dinner at Causeway, catch a movie and then grab some ice cream next door at White Farms.
This space is one of a kind. Check their website for which performances will be happening at the time of your stay.
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Rockport Music-Shalin Liu Performance Center
37 Main StThis space is one of a kind. Check their website for which performances will be happening at the time of your stay.
Excellent Hiking and scenery close by in Rockport for all ages.
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Halibut Point State Park
Gott AvenueExcellent Hiking and scenery close by in Rockport for all ages.
Boat building, free harbor walk, outdoor Seapocket Aquarium (with touch tanks) and the new Maritime Science Education Center with museum and store. Great for kids!
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Maritime Gloucester
23 Harbor LoopBoat building, free harbor walk, outdoor Seapocket Aquarium (with touch tanks) and the new Maritime Science Education Center with museum and store. Great for kids!
Cape Ann Art Haven
Sign up for classes. 20 Maplewood Ave unit B Gloucester, MA
A short drive away, Bearskin Neck in Rockport has many shops, restaurants and art to take in with stunning views of the ocean.
Bearskin Neck, Rockport, MA 01966, Verenigde Staten
A short drive away, Bearskin Neck in Rockport has many shops, restaurants and art to take in with stunning views of the ocean.
Wooded trails and stone walls. Take a map! Parking on Dogtown Rd. off of Cherry St. & Gee Ave.
Dogtown Commons, Gloucester, MA 01930, Verenigde Staten
Wooded trails and stone walls. Take a map! Parking on Dogtown Rd. off of Cherry St. & Gee Ave.
Gloucester Stage Company
267 E Main StProfessional live theatre
Charlie's Charters Fishing and Sightseeing
415 Main StPrivate Fishing charter
Hike & explore without leaving Gloucester! Part of a larger network of protected lands - Essex County's Land Trust provides ample green space throughout Gloucester. Check out the Greenbelt website for trail maps and detailed info on; Annisquam Woods, Back Shore, Carter Reservation, Gabriel and Selma Kleimola Reservation, Goose Cove Reservation, Harvey Reservation, Natti Woodland, Seine Field, Stony Cove/Presson Point and Tompson street Reservation.
Greenbelt Hiking Trail
Hike & explore without leaving Gloucester! Part of a larger network of protected lands - Essex County's Land Trust provides ample green space throughout Gloucester. Check out the Greenbelt website for trail maps and detailed info on; Annisquam Woods, Back Shore, Carter Reservation, Gabriel and Selma Kleimola Reservation, Goose Cove Reservation, Harvey Reservation, Natti Woodland, Seine Field, Stony Cove/Presson Point and Tompson street Reservation.
Wicked Pissah Fishing
Give Paul a call! He’s the best.
Brand new to Gloucester! Stage, studio, restaurant & bar all rolled into one. Walking distance from the house @ 177 Main Street.
The Cut - Stage • Studio • Restaurant • Bar
Brand new to Gloucester! Stage, studio, restaurant & bar all rolled into one. Walking distance from the house @ 177 Main Street.
Cape Ann Golf course in nearby Essex features a beautiful 9 hole course with sweeping views of conservation land and the backside of Crane Beach to the ocean and beyond. After the game, be sure to checkout the Fairway Pub for some delicious homemade Essex fare, open for lunch and dinner during the regular season. OPEN year round, weather permitting - sunup till sunset. This is a USGA Rated Course. Reservations accepted 7 days in advance.
Cape Ann Golf Course
99 John Wise AveCape Ann Golf course in nearby Essex features a beautiful 9 hole course with sweeping views of conservation land and the backside of Crane Beach to the ocean and beyond. After the game, be sure to checkout the Fairway Pub for some delicious homemade Essex fare, open for lunch and dinner during the regular season. OPEN year round, weather permitting - sunup till sunset. This is a USGA Rated Course. Reservations accepted 7 days in advance.
A challenging 9 hole course with clubhouse views of Sandy Bay and Rockport’s famous Twin Lights. 36 Country Club Road Rockport, MA. Open to the public during weekdays only.
Rockport Golf Club
36 Country Club RdA challenging 9 hole course with clubhouse views of Sandy Bay and Rockport’s famous Twin Lights. 36 Country Club Road Rockport, MA. Open to the public during weekdays only.
Constructed in 1906 by one of America’s first professional interior designers, Henry Davis Sleeper, the unsung yet remarkable waterfront Beauport/Sleeper-McCann House is a must visit.
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Historic New England Beauport Sleeper--McCann House
75 Eastern Point BlvdConstructed in 1906 by one of America’s first professional interior designers, Henry Davis Sleeper, the unsung yet remarkable waterfront Beauport/Sleeper-McCann House is a must visit.
Take a tour to see the 150-ton ice-making facility, including 300 lb ice blocks, ice sculptures, and to learn the history of the industry
Cape Pond Ice
104 Commercial StTake a tour to see the 150-ton ice-making facility, including 300 lb ice blocks, ice sculptures, and to learn the history of the industry
Gloucester Boat Rental
63 Rogers StreetGreat for a rainy day! Harbor 9 Golf is focused on providing year-round golf simulation experiences for golfers of all ages and skill levels. Food and adult beverages available. Check their website for hours of operation.
Harbor 9 Golf
Great for a rainy day! Harbor 9 Golf is focused on providing year-round golf simulation experiences for golfers of all ages and skill levels. Food and adult beverages available. Check their website for hours of operation.
Beaches
Our favorite local beaches
Our personal favorite especially for kids. Tidepools, long walks and rock climbing. Bathrooms and concessions are open during the season. Tip: Make sure to reserve your beach pass!
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Wingaersheek Beach
Our personal favorite especially for kids. Tidepools, long walks and rock climbing. Bathrooms and concessions are open during the season. Tip: Make sure to reserve your beach pass!
Halfmoon Beach
Western AveA little gem of a beach tucked into Stage Fort Park
Travel + Leisure named Good Harbor one of the best beaches in the US.
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Good Harbor Beach
Travel + Leisure named Good Harbor one of the best beaches in the US.
Small beach with free and convenient on-street parking.
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Plum Cove Beach
1000 Washington StSmall beach with free and convenient on-street parking.
This gem of Gloucester has it all...Half moon beach, a large playground for kids, walking trails, plenty of open green space with grills for your use. There is a large parking lot so if you didn't want to walk from The Chillavista you could park here as well. In the summer catch live music under the gazebo with food trucks and festivals
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Stage Fort Park and Beach
24 Hough AveThis gem of Gloucester has it all...Half moon beach, a large playground for kids, walking trails, plenty of open green space with grills for your use. There is a large parking lot so if you didn't want to walk from The Chillavista you could park here as well. In the summer catch live music under the gazebo with food trucks and festivals
Niles Beach
On a clear day you can catch a view of the Boston Skyline
This beach is a very short walk from the house! It’s a small and sandy beach that offers swimming, sunbathing & views of the boats in the harbor.
Pavilion Beach
This beach is a very short walk from the house! It’s a small and sandy beach that offers swimming, sunbathing & views of the boats in the harbor.
Graves Beach
Backed by trees, this sandy stretch of beach offers swimming, kayaking & scenic views
Cressy Beach
A rocky beach great for climbing and exploring
Spanning both Gloucester & Rockport. Rockport Rd. Gloucester, MA
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Long Beach Gloucester
44-30 Rockport RdSpanning both Gloucester & Rockport. Rockport Rd. Gloucester, MA
Folly Cove
Right on the Gloucester/ Rockport line this is a popular scuba diving spot.
Reizigersadvies
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St. Peter's Fiesta
This is a must! Watch the famed Greasy Pole event, seine boat races, kids carnival and so much more.
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Gloucester Blues Festival
Don't miss the jams!
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Gloucester Waterfront Festival
August. There will be over 250 booths featuring artists and craftsmen from all over the country, as well as live music, and delicious food including a lobster bake.
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Block Party
August. 6-10pm. Main Street.
Live music, street performers, al fresco dining, vendors, food vendors and more!
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Gloucester Juneteenth Festival
Sun, June 19, 2022 - 10:00 AM – 2:00PM
Cape Ann Museum Green
13 Poplar Street
Gloucester
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Rockport Jazz Festival
August
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Bluefin Blowout
Tuna Tournament as seen on "Wicked Tuna"
July
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Sunday Farmers Market
Magnolia Community Farmers Market. Sunday 10AM-1PM. 1 Lexington Ave Gloucester. Weather Permitting and seasonal. Experience, fresh local food and wares!
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Fishtown horribles Parade - July 3rd @ 6PM
6 p.m. from Gloucester High School, 32 Leslie O. Johnson Road, and follow its traditional route out Centennial Avenue, left on Western Avenue to Washington Street at Tally’s Corner, right down Washington and left onto Rogers Street, left on Manuel F. Lewis Street, then a left up Main Street and a right up Pleasant Street to Prospect Street, the left on Prospect, right on Railroad Avenue and a right onto Washington Street, finishing with a left onto Centennial Avenue back to Gloucester High.
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Food Truck Tuesdays @ Maritime Gloucester
In the summer from 4pm- 7Pm @ 23 Harbor Loop Gloucester. A rotating line up of food trucks! Museum, aquarium and museum store also open until 7pm. Seasonal.
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Harbor Loop Summer Concert Series
Free, fun and family friendly concert series on the water @ 1 Harbor Loop (behind the Fitz Hugh Lane House) Thursday’s from 5:30-9pm. Happening all Summer long.
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Music on Meetinghouse Green
The Gloucester Meetinghouse Foundation presents a series of 9 free Friday concerts on Meetinghouse Green, corner of Church and Middle St, Gloucester, from July to September. The family-friendly concerts begin at 6 pm. Bring folding chairs or blankets. There will be food vendors at every concert!
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Bandstand Summer Concert Series
Every Sunday night in the summer (7pm) at the bandstand in Stage Fort Park. Admission and Parking are free. Restrooms are ADA accessible. Bring a chair or a blanket!
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Movie Nights on the Lawn at Hammond Castle Museum
Thursday nights during the summer months. Doors open at 6pm, film begins at sundown (approx. 8pm.) Bring a blanket and a carry in/carry out picnic as these events are lawn seating only. Concessions will be sold. In the event of rain, the movie will be moved inside to the Great Hall. Check the website for up to date info and to see what movie is playing!
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Sidewalk Bazaar
August @ 9:00 Am - August 7 @ 5:00 Pm. The annual Sidewalk Bazaar takes place on Main Street in downtown Gloucester. Vendors, street food, live music, and children’s activities. Artists, Crafters, Food Vendors, Non-Profits, Kids Activities & Entertainers.
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Lobster Trap Tree lighting Ceremony
December. Don't miss the Lobster traps and buoys decorated by the children of Cape Ann Art Haven.
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Tree Lighting & Santa Holiday Parade
December. Entertainment, free refreshments, tree lighting and annual Santa parade. Kids can visit with Santa! Held in Kent Circle (Essex @ Western Avenue) Gloucester, MA.
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Winter Lights on Cape Ann
Running November - January 1st. 100+ displays of festive lights contributed by local business and their store fronts.
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“ Gloucester’s So Salty” Event
January @ Cape Ann Museum. Free admission. Come see ice sculptures, live music and food.
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Gloucester Schooner Festival
Labor Day weekend. Happening all over Gloucester.