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Calendar of Events

December 2022: Florida Keys Events

Image for COAST Is Clear Music & Arts Festival Image for COAST Is Clear Music & Arts Festival Image for COAST Is Clear Music & Arts Festival Image for COAST Is Clear Music & Arts Festival
Image for Pole Vault in Paradise Image for Pole Vault in Paradise Image for Pole Vault in Paradise Image for Pole Vault in Paradise
Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo Image for Big Pine & Lower Keys Nautical Expo
Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race Image for Hemingway 5k Sunset Run & Paddleboard Race
Image for Key West Half Marathon & 5k Image for Key West Half Marathon & 5k Image for Key West Half Marathon & 5k Image for Key West Half Marathon & 5k
Image for Key West Bicentennial Exhibit at The Custom House Museum
  • Mar 31, 2022 - Dec 11, 2022 Key West Arts & Culture
  • Key West Bicentennial Exhibit at The Custom House Museum
  • Website
  • Key West Art & Historical Society welcomes the public to view the ‘Key West 200’ exhibit at the Custom House Museum, 281 Front St. The exhibit is to highlight Key West’s people, culture and community beginning with the settlers and government officials who arrived on this remote island in early 1822, featuring rarely displayed artifacts. Divided by decade, the exhibit emphasizes many of the significant moments and people that have influenced so much of what we celebrate today.
Image for History of Diving Museum: Sponge Hunters
  • Oct 25, 2022 - Dec 31, 2022 Islamorada Arts & Culture
  • History of Diving Museum: Sponge Hunters
  • Website
  • Sponge Hunters: Key West Hookers, Bahamian Free Divers, and the Hard Hat Divers of Tarpon Springs will be on display May 19 through December 31, 2022. Learn about the sea sponge and its uses, from the long history of fishers to modern fisheries, current restoration efforts and the various dive methods used in seeking out this treasured aquatic animal. Mile marker 83 bayside, Islamorada. 10 a.m. - 5 p.m. daily except Thanksgiving, Christmas Day, and New Year’s Day.
Image for 2022 Harbor Walk of Lights
  • Nov 23, 2022 - Dec 31, 2022 Key West
  • 2022 Harbor Walk of Lights
  • Website
  • The “Harbor Walk of Lights” stretches along the seawall past Greene, William and Margaret Streets to the Key West Ferry Terminal. A nautical theme honors the maritime history of the Key West waterfront. The harbor walk area in the Historic Seaport glimmers with holiday displays throughout the season, all themed to celebrate the island city’s maritime heritage. Elements include tens of thousands of lights, dozens of lighted palm trees, a lobster trap holiday tree, a nautically decorated pine and a tree adorned with fishing buoys that resemble giant ornaments.
Image for Key West Holiday Fest
  • Dec 1, 2022 - Jan 1, 2023 Key West
  • Key West Holiday Fest
  • A merry range of celebrations during Key West's busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual hometown holiday parade, festive island lights tours via the Conch Tour Train and Old Town Trolley, seasonal artisan markets and bazaars, and New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”
Image for Key West Fishing Tournament
  • Dec 1, 2022 - Jul 31, 2023 Key West Fishing
  • Key West Fishing Tournament
  • Website
  • More than 40 species of fish are targeted during the multi-month tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.
  • Dec 1, 2022 - Jan 22, 2023 Islamorada Fishing
  • Florida Keys Gold Cup Sailfish Championship
  • 305-852-2102 Email Website
  • Anglers are to pursue sailfish, the most plentiful billfish in the waters off the Keys, in a series of three competitions - the Islamorada Sailfish Tournament, Dec. 1-4, 2022; the Islamorada Fishing Club Captain's Cup Sailfish Tournament, Jan.17-18, 2023; and the Cheeca Lodge Presidential Sailfish Tournament Jan. 20-22, 2023 - after which the Gold Cup is awarded.
Image for Key West Fishing Tournament
  • Dec 1, 2022 - Jul 31, 2023 Key West Fishing
  • Key West Fishing Tournament
  • Website
  • More than 40 species of fish are targeted during the multimonth tournament, with divisions for men, women, junior anglers (ages 10 to 15) and Pee Wees (under 10 years old). The Key West Fishing Tournament strongly encourages the release of game fish. All participating anglers receive certificates noting their catches and qualify for a variety of prizes.
Image for COAST is CLEAR Music and Arts Festival
  • Dec 1, 2022 - Dec 4, 2022 Key West Arts & Culture
  • COAST is CLEAR Music and Arts Festival
  • Website
  • Enjoy a weekend in the sun surrounded by close compadres — or simply folks you’ve only just met because of a shared love of music and art. The festival's main events are concerts at the festival grounds Saturday and Sunday. Two-day General Admission, VIP tickets and detailed information is available online. Festival is to be held rain or shine, at Fort East Martello, 3501 S. Roosevelt Blvd.
Image for Islamorada Sailfish Tournament
  • Dec 1, 2022 - Dec 4, 2022 Islamorada Fishing
  • Islamorada Sailfish Tournament
  • Website
  • The Florida Keys Gold Cup Sailfish Championship triple-crown series is to open with the Islamorada Sailfish Tournament, a primary fundraiser for the Islamorada Charter Boat Association Thursday, Dec. 1 through Sunday, Dec. 4. Social events are to be headquartered at the Whale Harbor Inn and Marina complex at mile marker 83.
Image for Florida Keys Holiday Fest
  • Dec 2, 2022 Islamorada
  • Florida Keys Holiday Fest
  • 305-664-4503 Website
  • The fun is set for 4-10 p.m. at the Founders Park beach area, mile marker 87. The crowd-pleasing celebration centerpiece, a 35-foot-tall holiday tree with “magical” snow blowing from its branches, is to be lighted at 6 p.m. Kids can frolic in a magical 30-ton snow mountain during the event. Parents can bid on one-of-a-kind Keys-designed ornaments during a silent auction and explore a holiday gift bazaar. Other activities include caroling, Santa's Sweet Shoppe with gourmet desserts and coffee, and a holiday parade at 7:30 p.m.
Image for Holiday Village & BeLighted Bike Ride
  • Dec 2, 2022 Key West
  • Holiday Village & BeLighted Bike Ride
  • Website
  • The Wesley House Family Services’ Holiday Village & BeLighted Bike Ride is a great family-friendly event to help kick off the holiday season. The Holiday Village from 4-8 p.m. features community and vendor booths, food trucks, a best bike contest at 7 p.m. and photos with Santa. The bike ride leaves at 8 p.m. Admission $15 adults, $10 children, kids 4 and under free. Find tickets, information and bike contest registration online.
Image for City of Key West Hometown Holiday Parade
  • Dec 3, 2022 Key West
  • City of Key West Hometown Holiday Parade
  • Website
  • Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Truman Avenue and White Street beside Bayview Park. Seeing Santa is a highlight for kids.
Image for Grand Opening: Plant a Million Corals
  • Dec 3, 2022 The Lower Keys Environmental
  • Grand Opening: Plant a Million Corals
  • Website
  • Plant a Million Corals invites you to a Grand Opening and Coral Cutting celebration Sat. Dec. 3 from 3 to 5 p.m. Take a tour of the new Restoration Park, see demonstrations of the coral restoration operation and meet the team. Founder Dave Vaughn will be signing copies of his new book, “The Secret Life of Corals: Sex, War, and Rocks that Don’t Roll.” The event is free to attend at 23801 Overseas Hwy, Summerland Key.
Image for Bethlehem in the Keys
  • Dec 3, 2022 - Dec 4, 2022 Marathon
  • Bethlehem in the Keys
  • Bethlehem in the Keys, a Christmas-themed dinner theater performance, will be performed at Marathon Community Church on Friday, Dec. 3rd. Doors open at 6 p.m., show starts at 7. There will be a matinee on Saturday, Dec. 4 with doors open at 2 p.m. and performance at 3. Tickets are $50 for dinner and $30 for the matinee. Call 305-481-7233 to reserve tickets.
Image for Friends of the Key West Library Book Sale
  • Dec 3, 2022 Key West
  • Friends of the Key West Library Book Sale
  • Website
  • The Friends of the Key West Library will hold the December Book Sale outside in the Library Palm Garden at 700 Fleming Street on Saturday, Dec. 3, from 10am-1pm. Most books are priced at $1, although for this sale, there is a nice selection of art books suitable for holiday gifts priced in the $10-20 range.
Image for Pet Pictures with the Grinch
  • Dec 3, 2022 Key West
  • Pet Pictures with the Grinch
  • Website
  • Bring your critters to Hank’s Hair of the Dog Saloon, 409 Caroline Street from 11 a.m. to 2 p.m. for pet pictures with The Grinch. Proceeds benefit River’s Wish, Inc., a non-profit senior dog sanctuary.
Image for Key Largo Shop, Jingle & Mingle
  • Dec 4, 2022 Key Largo
  • Key Largo Shop, Jingle & Mingle
  • Shop for gifts from local vendors and enjoy some holiday cheer from 11 a.m. to 4 p.m. at this annual event at the Cirque Salon Studios at Tradewinds Plaza, mile marker 101 oceanside in Key Largo.
Image for Key West Woman's Club Holiday Open House
  • Dec 4, 2022 Key West
  • Key West Woman's Club Holiday Open House
  • Website
  • Members have decked the halls of the historic mansion at 319 Duval Street for all to enjoy at Sunday's open house from 4 to 6 p.m. Enjoy appetizers, desserts and Amsterdam eggnog, and an appearance by Santa. Music from the Bahama Village Children's Choir and the Key West Community Orchestra. Official tree lighting by Mayor Teri Johnston. Donations of new, unwrapped clothes for students ages K-12 are appreciated.
Image for Key West Artisan Market: 10th Anniversary Edition
  • Dec 4, 2022 Key West
  • Key West Artisan Market: 10th Anniversary Edition
  • Website
  • Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and breathtaking ocean views as we celebrate 10 years of the Key West Artisan Market with old and new friends. Also supporting Friends of the Aids Memorial which is located across the street at White & Atlantic at the entrance to the Edward B. Knight Pier. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.
Image for Eaton Street Christmas Stroll
  • Dec 4, 2022 Key West Arts & Culture
  • Eaton Street Christmas Stroll
  • Website
  • Key West Theater, The Studios of Key West, St. Paul’s Episcopal Church, Tropic Cinema, Keys Choral Arts and the Key West United Methodist Church unite for the annual Eaton Street Christmas Stroll. Each venue hosts a short Christmas-themed performance with caroling as you walk from presentation to presentation. At The Studios of Key West, sip Christmas cocktails with a view and get an extra chance to catch the Members Show for some holiday shopping. The Stroll begins at 4 p.m. at St. Paul's.
Image for Full Moon Yoga
  • Dec 7, 2022 Islamorada Environmental
  • Full Moon Yoga
  • Website
  • Meditate and relax under the glow of the full moon and the twinkling stars at Postcard Inn, Islamorada from 6 to 7:30 p.m. Zenfully Aware Yoga, the Islamorada Resort Collection, and Coral Restoration Foundation™ are bringing you on an adventure – a yoga practice centered around how the full moon affects the coral reefs and the spawning and growth of the reefs as the lungs of the earth. 50% of all proceeds will be donated to Coral Restoration Foundation™. Non-guests may register online for $25; free for resort guests.
Image for Smuggling in the Florida Keys: Part IV
  • Dec 7, 2022 Islamorada Arts & Culture
  • Smuggling in the Florida Keys: Part IV
  • Website
  • The Florida Keys History & Discovery Center lecture series "Smuggling in the Florida Keys" Part IV, the final panel in the series, consists of State Prosecutor Allison DeFoor speaking on what it took to convict those who were involved in Smuggling in the Florida Keys, along with Richard "Dickie" Lynn, who served over 30 years in federal custody and was granted compassionate release by a federal judge in 2021. Doors open at 5 p.m. to explore the museum with light appetizers and cash bar available. Presentation 6-7:30 p.m. Advance registration required, $10.
Image for Nutcracker Key West
  • Dec 7, 2022 - Dec 11, 2022 Key West Arts & Culture
  • Nutcracker Key West
  • Website
  • A unique subtropical version of the classic holiday ballet "The Nutcracker" awaits Keys visitors, flavored with characters and settings that depict Key West's colorful history, vibrant coral reef environment and even free-roaming local roosters. Blending professional dancers and local talents, the production features exquisite costumes and sets inspired by island lore. Performances take place at the Tennessee Williams Theatre at 5901 College Road.
Image for Friends of the Key West Library 50th Anniversary Celebration
Image for Tropical Holiday Fun Fest
  • Dec 9, 2022 Marathon
  • Tropical Holiday Fun Fest
  • Website
  • Come out to Marathon Community Park for a night of Holiday fun. Enjoy live holiday music, entertainment by the Marathon Community Theater dancers and the Prodigy Dancers, face painting, bounce houses, cotton candy and other treats, and see Santa! Mile marker 49 oceanside.
Image for "Ocean to Everglades: Stories of the Sea" Film & Discussion
  • Dec 9, 2022 Islamorada Environmental
  • "Ocean to Everglades: Stories of the Sea" Film & Discussion
  • Website
  • Join Surfrider Florida Keys and Sereia Films on Friday, December 9th for "Ocean to Everglades: Stories of the Sea" - a night of film screenings and discussion on sustainable seafood in Florida and the ocean livelihoods that depend on it. Happy hour will be from 6:30 to 7 p.m., film screening from 7 to 8:15, followed by a panel discussion on sustainable seafood in Florida and the Keys. Mile marker 80.5 bayside. Online advance registration required.
Image for Holiday Historic Inn Tour
  • Dec 9, 2022 Key West
  • Holiday Historic Inn Tour
  • Website
  • During this enchanted Friday evening, visit and tour four beautifully decorated island locales: Key West Butterfly & Nature Conservatory, The Mermaid & the Alligator, Winslow’s Bungalows, and Weatherstation. Explore the unique architecture and history at each stop while enjoying sweet and savory holiday treats and libation samplings. Limited trolley transportation will be provided between properties, but participants are encouraged to bike, walk or use their own transportation. Purchase tickets online, then pick up tickets after 5 p.m. on Dec. 9 at Butterfly & Nature Conservatory. Tour between 6 and 8 p.m.
Image for Eighth Annual Islamorada Half Marathon & 10K, Rumrunner 5K  and Beach N' Beer Mile
  • Dec 10, 2022 - Dec 11, 2022 Islamorada
  • Eighth Annual Islamorada Half Marathon & 10K, Rumrunner 5K and Beach N' Beer Mile
  • Website
  • Whether bucket-list runners or newbies, participants of all ages and skill levels are invited to register for the subtropical footrace. In the Beach N’ Beer Mile, runners must consume four beers over a 1-mile course in Islamorada. Organizers said the best time to beat for the event is seven minutes. Cash prizes are to be awarded the top three male and female half-marathon finishers, as well as awards for the top three finishers of the 10k.
Image for Ninth Annual Florida Keys SPCA Parade of Paws
  • Dec 10, 2022 Key West
  • Ninth Annual Florida Keys SPCA Parade of Paws
  • Website
  • Join the Florida Keys SPCA at the Higgs Beach Dog Park in Key West from 10 a.m. - 2 p.m. for a family-friendly, fun-filled day of live music, local vendors at the Holiday Bazaar and the crowning of the 2022 Royal Court.  Enjoy pictures with Santa, sloppy kisses at the Kiss A Bull booth, fun raffles and a dog parade where all pups are welcome to strut their stuff around the beach!  Costumes encouraged!  All proceeds from the event will benefit the homeless animals of the Middle and Lower Keys.
Image for Pops in the Park: Keys Community Concert Band Holiday Concert
Image for Key Largo Boat Parade - A Cartoon Christmas
  • Dec 10, 2022 Key Largo
  • Key Largo Boat Parade - A Cartoon Christmas
  • Key Largo's annual holiday boat parade on Blackwater Sound lights up the night beginning at 7:30 p.m. Saturday, Dec. 10 with boats decked out for the holidays. Watch from waterfront locations including various restaurants and nightspots such as Caribbean Club and Jimmy Johnson's Big Chill - both at MM 104 bayside - as well as the public Rowell's Waterfront Park.
Image for Key West Triathlon
  • Dec 11, 2022 Key West
  • Key West Triathlon
  • Website
  • The Key West Triathlon challenges participants to swim in the waters of the Atlantic Ocean, bike along a portion of the Florida Keys’ scenic Overseas Highway and run on a fast, flat course beside the Atlantic. As well as the Olympic-distance and sprint-distance triathlons, Aquabike and sprint duathlon competitions are featured. Higgs Memorial Beach Park, 1000 Atlantic Boulevard, Key West.
  • Dec 16, 2022 - Dec 18, 2022 Islamorada Fishing
  • Islamorada Junior Sailfish Tournament
  • Tammy Gurgiolo 305-240-9337 Email
  • The Florida Keys’ oldest sailfish tournament for kids age 16 and under, this event has been held since 1964. Hosted at the Coconut Palm Inn, mile marker 92 bayside.
Image for The 12 Days of Christmas: Burlesque Show Spectacular
  • Dec 16, 2022 - Dec 17, 2022 Key West LGBTQ
  • The 12 Days of Christmas: Burlesque Show Spectacular
  • Website
  • This extravaganza, based on the classic Christmas song, combines the talents of world class burlesque performers, circus style entertainers and singers. The cast, lead by Julliard School graduate Shelly Watson along with all your favorite Key West Burlesque dancers, is sure to dazzle audience members. Doors open at 7 p.m., show at 8. Tickets $45 to $100, available online. Key West Theater, 512 Eaton Street.
Image for Holiday Historic Inn Tour
  • Dec 16, 2022 Key West
  • Holiday Historic Inn Tour
  • Website
  • Visit and tour four beautifully decorated island locales: Hemingway’s Library at Papa’s Pilar Distillery, The Marquesa Hotel, The Gardens Hotel, and Island City House, and explore their unique architecture and history while enjoying sweet and savory holiday treats and libation samplings between 6 and 8 p.m. Purchase tickets online, then pick them up after 5 p.m. on the night of the tour at the first property, Hemingway’s Library at Papa's Pilar Distillery. Participants will need to walk, bike or use their own transportation between locations.
Image for 14th Annual 5K Rudolph Red Nose Run
  • Dec 17, 2022 Key West
  • 14th Annual 5K Rudolph Red Nose Run
  • Website
  • Don your festive holiday jammies and join! Starts and ends at Southernmost Beach Café, 1405 Duval St. Race day check-in starts at 7 a.m. with 8 a.m. start time. After the race, enjoy refreshments, prizes and a fabulous silent auction. Pre-race packet pickup is Friday, Dec. 16 from 5-7 p.m. at the Café. Runners and walkers of all ages and abilities are welcome to participate. Registrants receive a free t-shirt; prizes for most festive and unusual PJ’s. Presented by nonprofit group, A Positive Step for Monroe County.
Image for Marathon Latin Festival
  • Dec 17, 2022 Marathon Arts & Culture
  • Marathon Latin Festival
  • Website
  • Hosted by Baby Lores, one of the pioneers in the Cuban music scene, this all-day music fest is from 10 a.m. to 10 p.m. at Marathon Community Park at mile marker 49. Enjoy family-free entertainment and activities during the day and a grand fiesta of music from 5 to 10 p.m. by several dozen top Latin musical entertainers. Partial proceeds from this event are to support the Somos Esperanza foundation, that helps provide for sick children, providing necessary medical attention and equipment. Advance purchase tickets are online for $50 per adult, $25 for ages 13-21, with kids 12 and under free. VIP tickets also available. Tickets are also to be on sale the day of the event.
Image for Key West Botanical Garden Native Plant Sale
  • Dec 17, 2022 Key West
  • Key West Botanical Garden Native Plant Sale
  • Website
  • The plant nursery offers native Florida trees, shrubs, vegetables and vines for sale from 9 a.m. to noon the third Saturday of the month. Master Gardener volunteers will be on site to help answer any plant questions. There are 165 species of plants available with an inventory totaling more than 2,000 plants that attract birds and butterflies in 1-gallon to 10-gallon pots. Key West Botanical Garden members receive a discount. The Garden, located at 5210 College Road on Stock Island, is a 501 (c) 3 non-profit corporation and all proceeds directly benefit the Garden’s conservation program.
Image for Winter Wonderland at Crane Point
  • Dec 17, 2022 Marathon
  • Winter Wonderland at Crane Point
  • Website
  • There's a forecast for snow in the tropical forest at Crane Point Hammock Museum & Nature Trail during Winter Wonderland from 4:30 to 7:30 p.m. Bring the entire family to encounter reindeer ponies, holiday decorations, Santa and snow! Enjoy Santa stew, the chocolate fountain, roasted chestnuts and adult beverages for purchase. 5550 Overseas Highway, Marathon.
Image for Key West Lighting of the Menorah
Image for Key West Artisan Market: Shop Local Edition
  • Dec 18, 2022 Key West
  • Key West Artisan Market: Shop Local Edition
  • Website
  • Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, wide variety of food & libations, local musicians & authors and splendid ocean views as we offer everything you need to cross off your holiday shopping list. Supporting the Key West Shop Mom & Pop and #shoplocalkey west movement to keep our resources right here in our community. From 10 a.m. to 2 p.m., Sonny McCoy Indigenous Park, 1801 White Street.
Image for Old Island Restoration Foundation's Home Tours "Holiday Style"
  • Dec 28, 2022 - Dec 29, 2022 Key West Arts & Culture
  • Old Island Restoration Foundation's Home Tours "Holiday Style"
  • Website
  • The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating back to 1960. This 63rd series of tours features self-guided tours of homes festively dressed for the holidays on Dec. 28 and 29. After the holidays, home tour dates are Jan. 13-14, Feb. 17-18, and March 17-18. Tickets purchased online in advance are $45 for members, $55 for non-members and $60 at the door. Visit the website or call 305-294-9501.
Image for New Year's Eve Shoe Drop Celebration
  • Dec 31, 2022 Key West
  • New Year's Eve Shoe Drop Celebration
  • Email Website
  • The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.
Image for New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Dec 31, 2022 Key West
  • New Year's Eve: Conch Shell Drop at Sloppy Joe's
  • Website
  • The arrival of 2023 is to be heralded on the island's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval. Spectators gather on Duval for the annual gala, emceed by a rooftop host and featuring dancing in the street and a countdown to midnight recorded on a huge clock.
Image for New Year's Eve: Pirate Wench Drop at Schooner Wharf
  • Dec 31, 2022 Key West
  • New Year's Eve: Pirate Wench Drop at Schooner Wharf
  • Website
  • For piratical partiers, a New Year's Eve salute to Key West's rowdy seafaring roots is scheduled at the island's Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome 2022. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.
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