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Fall Activities Round-Up: October 2018 Calendar of Harborside Events

Post by Amanda Jones - Published on 9/12/18 6:11 PM

Boaters, welcome to October! As much as we love the summer, we are officially ready for the bats & boos that this spooky month is filled with. 

Hearty New Englanders know there's no better way to see the fall foliage than from the water, and boaters across the country can make the most of October as well by heading to harborside events. Find a haunted shipyard, pumpkin flotilla, apple festival, Oktoberfest, or costumed regatta near you!

Jump to your region: East Coast | Inland Waterways | Florida & The Keys | Gulf Coast | The Great Lakes | West Coast | The Islands

Still looking for those fun September events to do with your crew? Click here

Know of events happening in your area for the months of  November or December? Get in touch: Tweet at us, message us on Facebook, or email amanda.jones@dockwa.com


East Coast


  • NEW Portland – 

    • October 6: Wine Sail. A gorgeous scenic sail, with different options of wine, on board the 74-foot Sailboat, Frances.

    • October 7: Portland Harvest Festival. A family-fun celebration of Fall with live music, food, and activities for the entire crew. 

    • October 16: Harvest on the Harbor 2018. The Festival brings food lovers together for unique experiences that encompass Portland's culinary culture. 

    • October 21: The 4th Annual Portland Lantern Walk. This is a public art series taking place in Deering Oaks Park. 

  • NEW Rockland – October 19: Singing the Sea: A Concert of Maritime Songs. This is the final concert of the Rockland Folk Arts 2018 season. 

  • Damariscotta – October 5 - 8: Damariscotta Pumpkinfest & Regatta. This festival is in celebration of pumpkins with events taking place all throughout Columbus Day Weekend. The Pumpkinboat Regatta will take place at noon on Monday! 


  • NEW Burlington – 

    • October 21: The 1st Annual L.L.Bean Flannel 5K

    • October 28: The 8th Annual Burlington Halloween Bike Ride. There will be sweet prizes for the best group, the most clever, the scariest, and the best use of bicycle. AT the end there will be delicious pizza, music, prizes, and the awards ceremony! 

    • October 28: The 4th Annual Trick-or-Treat Street. Celebrate Halloween in downtown Burlington from 1-4 PM. Kids of all ages are invited to come down to The Church Street Marketplace in costume for free trick-or-treating and Halloween activities.  

  • Barnet – October 6: The 15th Annual Rubber Ducky Derby. An annual fundraiser for Ben's Mill, an old water powered mill that is being restored to a working museum. There will be tours of the mill, food available and a kid's table.   

  • Jay – October 14: The 8th Annual Bean & Brew Festival. Jay Peak's annual Festival features some of the finest locally-roasted coffees coupled with New England's finest beers.  

Find Dockage in Vermont

New Hampshire: 

  • NEW Portsmouth 

    • October 7: Wicked Haunted Waterfront Tour. Explore the darker past of Portsmouth on this haunted history tour. Seek out the shadows of shanghaied sailors and uncover the city's sordid past. 

    • October 20: Pumpkin SMASH. Pick a pumpkin from the pile, choose from an array of mallets, or two-by-fours and swing away! 

    • October 20: Crawl of Screams - Portsmouth. This Halloween dress how you like and be whoever you want at the Crawl of Screams. 

    • October 26 - 27: Ghosts on the Banke. Come and meet the Ghosts on the Banke at Strawbery Banke's famous Halloween celebration. Long-dead sea captains, 17th century shopkeepers and wayward pirates haunt the streets and houses of Portsmouth's oldest neighborhood as you trick-or-treat safely from house to historic house. 

    • October 30: Historic Portsmouth Legends & Ghosts Walk. An evening walk to some of the most historic and haunted locations in downtown Portsmouth. Hear about the Phantom of the Music Hall, strange tunnels and the unusual secrets hiding underneath Portsmouth streets and basements. Each guest will receive a trick or treat goody bag with either a trick or a treat inside! 

    • October 31: Portsmouth Halloween Parade. Marching into its 24th year, the Portsmouth Halloween Parade is a grassroots, all-inclusive celebration of community, creativity, and free expression that walks, stalks, dances, and trumpets through downtown! 

  • Goffstown – October 14: The 4th Annual Goffstown Pumpkin Regatta 10K. The race begins at 8:30 AM followed with a post race celebration at the Village Trestle and the last part of the day will consist of the Pumpkin Regatta where Giant pumpkins are turned into boats and raced down Glen Lake. 

  • NEW Milford – October 5 - 7: The 29th Annual Milford Pumpkin Festival. Signature festival events include: The Beer & Wine Tasting tent, a spectacular Fireworks show, two stages of live music and entertainment all weekend, the Giant Pumpkin Weigh-in contest, bounce house, carnival rides and so much more. 

  • NEW Dover – October 6: Apple Harvest Day. A day-long family event, featuring more than 400 crafters, delicious food, live music and entertainment, etc. The 5K road race starts at 8:30 AM on River Street.  

  • NEW Center Sandwich  October 6 - 8: The Annual Sandwich Fair. A full weekend of entertainment for the whole family. Events include Horse Pulling and Oxen competitions, exhibitions of goats, sheep, rabbits and poultry. The exhibit halls will be full of canned goods, baked goods, flowers and veggies. There will also be a Skillet Toss and a Keg Toss! 

  • NEW Berlin – October 13: The Annual RiverFire Festival. Burning brighter and hotter than ever with hundreds of jack-o-lantern's and bonfires illuminating the river, the spectacular annual RiverFire Festival will set the Androscoggin River ablaze at dusk! 

  • NEW Concord – October 19 - 20: Enchanted Forest. A family-friendly event for ages 4 to adults. Follow the enchanted trail into the nighttime forest illuminated by real jack-o-lanterns. Encounter larger-than-life creatures and characters as they present skits about mysterious activities in nature. 

  • New North Conway – October 19 - 28: Pumpkin Patch Express. All departures are from the North Conway Station for a leisurely round-trip train ride aboard vintage coaches to the White Mountain Cider Company where each child can visit the Pumpkin Patch and select their own pumpkin. 

  • NEW Holderness  October 27: Halloween Hoot N' Howl. 40-minute guided tours will depart every 10 minutes, bringing guests around a Halloween-themed trail. Along the way, guides will stop for guests to watch skits and other spooky attractions. 


  • NEW Boston –

    • October 1 - 31: Pirate Harbor Cruise. Tour Boston Harbor aboard a pirate ship! 

    • October 1 - 31: Ghosts & Gravestones Tour. A 90-minute spine-tingling walking tour of two of Boston's oldest burying grounds. 

    • October 1 - 6: Boston Fashion Week. An annual celebration of Boston style featuring a great wealth of local talent. 

    • October 3, 5, 10 & 12: Seaport Sweat 2018. Boston's free outdoor workout series. 

    • October 6 - 7: Boston Occupied: An Insolent Parade. An reenactment of the landing of British troops in Boston 250 years ago. 

    • October 7: Ben Howard will be performing at the Blue Hills Pavilion

    • October 7: BAA Half Marathon. Presented by the Dana-Farber Cancer Institute. 

    • October 8: Reebok Boston 10K for Women

    • October 13, 20 & 27: B.A.R.K. in the Park. Join National Park Rangers for a half-mile walk from Carson Beach to Dorchester Heights, followed by tips, treats and fun. 

    • October 19: The Fall Pumpkin Float. This event features floating pumpkins, kids' activities, and music at Boston Common Frog Pond. Bring a hollow pumpkin under 8 inches in diameter & watch as it floats in the pond! 

    • October 20 - 21: Head of The Charles Regatta. Since its origin in 1965, the Head Of The Charles Regatta has welcomed the world's best crew teams to the banks of  the Charles River for the ultimate two-day rowing competition. 

    • October 27: Haunted Hotel Halloween Party. W Boston invited scream seekers to the highly anticipated Haunted Hotel. Guests will check into this unforgettable affair and enter a dark and twisted fantasy where luxury takes a sinfully wicked turn. 

    • October 27: Halloween Pet Parade. Dress up your pet and parade around Faneuil Hall Marketplace then walk the red carpet in front of a panel of judges. 

    • October 31: The Black Pearl Haunted Cruise. The Spirit of Boston will have four decks, three DJS and two floors of music for you to monster mash the right way. Enjoy a three-hour sail with views of the Boston skyline too. 

Find Slips around Boston Harbor


  • Wellfleet – October 13 - 14: Wellfleet OysterFest. The Oyster festival is an annual celebration of the town's famous oysters, clams and its deep-rooted shellfishing traditions. 

  • East Falmouth – October 13: The 7th Annual Cape Cod Brew Fest. Sample beer from over 100 brewers while enjoying live music, food trucks, and dozens of additional vendors. 

  • Princeton – October 13 - 14: The 35th Annual AppleFest at Wachusett Mountain. This is Wachusett's most popular fall festival which celebrates over 100 craft exhibitors, a farmers' market, kids entertainment and some beautiful fall foliage. Enjoy live music, Apple Pie Baking and Eating Contests, and the Giant Pumpkin Weigh off. 

  • New New Bedford – 

    • October 13: NB Oktoberfest 2018. This Oktoberfest will feature a variety of local and national brews, food vendors and entertainment throughout the day and into the night. (Want to find out where other Oktoberfests will be this October? Check out our recent post, Oktoberfests by Boat

    • October 23 - 25: The Great Pumpkin Parade. Visit the grounds of the RJD to see a display of Jack-O-Lanterns, carved with care by community members. Inside the mansion, children can participate in a scavenger hunt with prizes. 

  • Quincy – October 5, 6, 7, 12, 13, 14, 18, 19, 20, 21, 25, 26, 27, 28 and 31: Ghost Ship Harbor. A haunted house attraction located deep in the Quincy Shipyard. There is an activation area where you can find food, entertainment, a bar, tarot card readings, midway games, VR experiences and more. The main attractions take place on the deck of a 716 foot destroyer (battleship). 

Rhode Island: 

  • NEW Newport –

    • October 1, 8 & 15: VX One Monday Night Series. Enjoy VX One Racing hosted by the IYAC. 

    • October 4 - 8: The 4th Annual Rogue Island Comedy Festival. There will be 15 stacked shows across 5 nights, featuring over 50 stand-up comics from Comedy Central, The Tonight Show, The Late Show, HBO, Netflix, SNL, and more. 

    • October 5 - 7: The 2018 New York Yacht Club Global Team Race Regatta. Teams from England, Ireland, Italy, Australia, Argentina, Germany, Japan, the Netherlands and the United States will gather at Harbor Court for a two-on-two team race designed to showcase the international appeal and spectator-friendly nature of team racing. 

    • October 5 - 8: Bowen's Wharf Columbus Day Sidewalk Sale. Make your way to the waterfront for specials at the local shops. 

    • October 6: The 2018 Broadway Street Fair. The Street Fair will begin at Equality Park and extend all down into Washington Square. The day will be filled with music, food, family activities, exhibiting artists & makers and local non-profits. 

    • October 6: Beach Cleanup at Second Beach. Lend a hand, care for the land on Saturday from 12-2 PM. 

    • October 7: Newport Marathon and Half Marathon. This seaside course showcases the best views of Newport. 

    • October 10: Ales for Animals. Enjoy a fresh brew with your furry friend on the outdoor pavilion from 5 - 8 PM. For each beer sold, Newport Craft will donate $1 to the Potter League for Animals.

    • October 11: Women in Business After Hours. Join for a networking over food and wine for the fall Women in business event, featuring special guest speaker, Catherine Zipf. 

    • October 12: Newport Harbor Trash Skimmer Tour. Join Clean Ocean Access to learn about how the city of Newport is trying to clean up marine debris. The four Marina Trash Skimmers in Newport, have removed a combined 30,000 pounds of debris over the past two years from harbors and marinas on Aquidneck Island. 

    • October 13: 3-Hour 12 Meter Racing Experience. 12 Meter Charters gives people the opportunity to sail and race aboard America's Cup 12 Meter yachts that raced in the America's Cup. 

    • October 13 - 14: The 28th Annual Bowen's Wharf Seafood Festival. Honoring the harvest of the sea, this Festival offers fresh local seafood, continuous live music and family fun. 

    • October 17: Women's Adventure Film Tour - Newport RI. This tour is a celebration of the fantastic women around us who are doing extraordinary things. The films are to be enjoyed by women and men for all ages. 

    • October 20: Gooseberry Autumn Artisan Festival. An event for the whole family. There will be a ton of arts and craft vendors, children's events such as pumpkin painting, food and live music. 

    • October 21: The 8th Annual Citizens Bank Pell Bridge Run. This is a 4 mile run/walk over the famed Newport/Pell Bridge. This is the only day of the year that pedestrians are able to cross this iconic bridge on foot! 

    • October 24: NRF'S Golden Birthday. The Newport Restoration Foundation's 50th Birthday. Celebrate the work that has been accomplished and the exciting road ahead with light refreshments. 

    • October 12, 13, 19, 20, 26 & 27: The Fortress of Nightmares at Historic Fort Adams. Fortress of Nightmares are four haunted attractions inside North America's largest coastal fortification. Tunnels of Terror is a maze of Halloween horrors built deep inside the tunnels beneath Fort Adams. Mayhem 3D is a UV enhanced dark walk through haunted maze staffed with scare-actors. Rising Spirits is a presentation of Haunts for the Homeless and Paranormal360 is a 360 degree synchronized video experience, linked with special effects and unexpected frights. 

Find Dockage in Newport

  • Middletown –

    • October 6, 13, 20 and 27: The Saturday Farmer's Markets at Newport Vineyard. On Saturday morning from 8:30 - 12:30 PM check out the Aquidneck Growers' Market held outdoors on Newport Vineyards grounds. 

    • October 26: The 3rd Annual Halloween CarnEvil Celebration at Newport Vineyards. A premier costume party with an evening full of Circus Dynamics jugglers, TEN31 performers, DJ Jay Buff from 92 PRO-FM and prizes for best costume. 

    • October 27: The 3rd Annual Harvest Festival at Newport Vineyards. This is a day full of grape stomping, wine and Taproot beer tasting, and pie eating goodness. Enjoy live music, alcohol and food. There is even a Grape Stomping Competition and a Pie Eating Contest. 

  • NEW Portsmouth –

    • October 1 - November 4: Escobar's Highland Farm Corn Maze. Go get lost in the 8 acre corn maze! 

    • October 13: Beach Cleanup at Corys Lane from 12-2 PM.

    • October 14: The 2018 Heart & Sole Walk for the Animals. Animal lovers and their dogs are invited to enjoy a 1 or 2 mile walk and celebration at Glen Park to benefit homeless animals. 

    • October 25: The 2nd Annual Hallowine at Greenvale Vineyards. Join Clean Ocean Access at Greenvale for a wine tasting, light hors d'oeuvres and live music. 

  • Block Island – October 7: The Block Island Half Marathon

Find Slips in Block Island

  • Bristol –

    • October 1: Audubon Society: Citizens Bank Free Family Fun Day. Enjoy crafts, nature stories, animal discoveries, hikes and more. 

    • October 4 - 25: Hauntings of Linden Place Guided Tours. A one-hour tour of the Lind Place Mansion. Learn about the rumored hauntings of Colt Farm and Colt Memorial School, about vampires roaming the towns of Rhode Island in the 1800s and much more. Enjoy light refreshments after. 

  • Warren – October 7, 14, 21 and 28: Schoolyard Market at Hope & Main. Come grab great summertime treats for breakfast, lunch or dinner from the farmers market! 

  • NEW Providence –

    • October 4 - November 4: Jack-o-Lantern Spectacular at The Roger Williams Park Zoo. This year's show includes more than 5,000 intricately carved pumpkins featuring scenes of wizards, fairy-tales, and the luminaries of great myths and legends, alongside superheroes, and historical figures who changed our world. Revel in the sights and sounds of the season at the spectacular.  

    • October 6: The 26th Annual International Oktoberfest. Taking place at Bold Point Park on the East Providence waterfront, this event brings together dozens of seasonal, craft, imported and local brews, autumnal libations, food trucks, and a lively backdrop of entertainment. 

    • October 6 - 8: Federal Hill Columbus Weekend Festival. The Federal Hill Commerce Association will be hosting its Annual Columbus Day Weekend Festival on historic Federal Hill in Providence. The Annual Columbus Day Parade will take place on October 7 at 11 AM. 

    • October 11: Taste of Rhode Island. An original fundraising event at Roger Williams Park Botanical Center that brings together a number of Rhode Island's top chefs and caterers to offer attendees a taste of Rhode Island.

    • October 17 - 18: Commercial Marine Expo 2018. A trade show happening at the Rhode Island Convention Center with commercial vessel owners and operators, tug/tow owners and operators, fishing vessel owners and operators, harbormasters, boat yard operators, etc. 

    • October 19: The Malted Barley Oktoberfest. Enjoy beer at The Malted Barley in Providence along with a stein hoisting competition! 

    • October 27: Halloween at the Castle. Celebrate Halloween at Barnaby Castle with an open bar, food, entertainment, a costume contest and more! The event raises funds to support Barnaby Castles restoration. 

  • South Kingston – October 11: Food Truck Night at Sons of Liberty. Children and families are welcomed and encouraged to attend and enjoy the food trucks and outside activities. 

  • NEW Tiverton – October 5: Jack O' Lanterns in the Garden. An evening stroll through the Sandywoods Community Garden trail. The garden will be decorated with Jack-O'-lanterns, autumn and Halloween themes. The pumpkins will be illuminated from 6-8 PM. 

  • NEW Narragansett –


  • NEW Mystic – 

    • October 6 - 8: Chowder Days. What better way to enjoy the cool fall days than with a hot bowl of chowder at the Mystic Seaport Museum! Head on over and enjoy a variety of chowders and fall food favorites during Columbus Day Weekend. 

    • October 12, 13, 19, 20, 26, 27 & 28: Nautical Nightmares: Madness on the Mystic River. Join for an evening of haunted thrills with Nautical Nightmares. In this frightening theatrical, Mystic is falling into chaos. You will join the alienists of Arkham to investigate a haunted whaleship and the madness that has descended through the town. 

    • October 12: Mystic Pirate Invasion. Join with your fellow pirate lovers in Downtown Mystic for a weekend of pirate-themed fun. 

    • October 13: Oktoberfest 2018 Party at The Engine Room. Have a taste of German food and drink specials along with a Stein holding contest, live band, and did we mention German beers? 

    • October 18 - 21: The Mystic Film Festival. Enjoy the films at the first annual Mystic Film Festival. 

    • October 27:  Sea Scare. This Halloween, see the dinosaurs get in the spirit with a special trick-or-treat trek through the Dino trail at the Mystic Aquarium. 

  • New Fairfield – October 5 - 7: The 2018 Roger Punzi Memorial Regatta put on by the Candlewood Yacht Club. 

Reserve in Connecticut

New York: 

  • Centerport – October 6: The 38th Annual William K. Vanderbilt II Memorial Cup Race presented by Centerport Yacht Club and the Vanderbilt Museum. 

  • New York City, New York 


    • Pier 17 Rooftop Concert Series

      • October 5: Slash featuring Myles Kennedy and The Conspirators

      • October 6: Pink Martini

      • October 7: Paul Anka Sings Frank Sinatra

      • October 12: Thievery Corporation 

Find Dockage in New York


  • NEW Annapolis – October 27 - 28: The Halloween Howl Regatta presented by the Annapolis Yacht Club. 

  • NEW Pasadena – 

Reserve in Maryland


  • NEW Cape Charles – October 27: The 4th Annual Trick or Treat on the Creek. Hosted by The Oyster Farm Marina from 5-8 PM. Enjoy pumpkin painting, trick or treating and a best decorated boat contest! 

North Carolina: 

  • Bath –  October 19 - 20: Check out the Tricentennial of the notorious Blackbeard. The Town of Bath and the Greater Bath Foundation proudly observe the Tricentennial of Blackbeard, his crew, and their families who bravely established North Carolina's oldest town, the state's first port, its oldest standing brick church, and the foundations of our nation. 


Florida & The Keys

  • Naples – October 26 - 28: Naples Stone Crab Festival. The Festival will offer plenty of fresh stone crab claws, music, events, art and a ton of other fun activities for the whole family. 

  • West Palm Beach – October 28: The Fall Festival Regatta presented by the Palm Beach Sailing Club. 

  • Clearwater   October 18 - 21: The 39th Annual Clearwater Jazz Holiday. This is a four-day and four-night, world-class, live, music festival that takes place every third week of every October. 

Find Slips in Florida

Gulf Coast


Find Slips in Louisiana


West Coast:


  • Huntington Beach – October 20 - 21: BeachFront Cinema. Enjoy popular films on the Huntington State Beach. 

  • Newport Beach – October 5 - 7: Newport Beach Wine and Food Festival. Try tastes from 15 different gourmet restaurants each day and sip 200 different types of wines from 60 wineries while enjoying live music. 

  • Long Beach – October 4 - November 2: Dark Harbor. This haunted ship consists of 7 different haunted mazes, monsters, a 4D theater, immersive attractions, entertainment onstage, themed bars, and a concession food stand aboard the Queen Mary. 

  • Santa Monica – 

    • October 3 & 7: Twilight on the Pier. Free concerts taking place on the Santa Monica Pier. There will be great music performances plus food, a beer and spirits garden, games, and other activities. 

    • October 6: Off the Hook Seafood Festival. The festival will include seafood tastings from local restaurants, curated cocktails, live music, chef demos, games, and a beer garden. 

  • Hollywood – October 4 - 7: Shriekfest. This is an international horror and science-fiction film festival competition taking place at Raleigh Studios. 

  • San Francisco –

    • October 1 - 28: San Francisco Bay Cruise Adventure. Enjoy a one-hour scenic ride from Pier 39, under the Golden Gate Bridge, and then around Alcatraz. 

    • October 1 - 8: Fleet Week. Taking place over three consecutive days in the skies above the City's waterfont. An air show event that attracts over a million people around the bay. 

    • October 20: San Francisco's Wharf Fest. Featuring live music, street performers, craft and food vendors, a chowder contests, kids' rides, ship tours, and fireworks. 

  • Oakland – October 18 - 20: Autumn Lights Festival. This festival features illuminated art, fire dancers, art installations, live music, and interactive arts. 

  • Calabasas – October 20 - 21: Calabasas Pumpkin Festival. Enjoy live bands, a DJ dance zone, vendors, pumpkin food and beer, pumpkin painting, professional pumpkin carvers, kids' games and inflatables. 

  • Santa Rosa – October 20: Floating Pumpkin Patch. Hunt for your perfect pumpkin in the pool and then deck it out at the decorating station with all sorts of fun crafts. 
  • Los Angeles – October 6: Los Angeles County Dragon Boat Festival on Legg Lake. Watch dragon boat races, shop food vendors and see stage shows such as Chinese acrobats, live music, and dance performances. 


    Reserve in California


  • Seattle –

    • October 5 - 6: The Great Pumpkin Beer Festival. Enjoy 80 pumpkin beers, a marching band, a DJ and food trucks. 

    • October 5 - November 3: Haunted House at Georgetown Morgue. The Georgetown Morgue is a facility for tragic stories of death. The morgue has a history of thousands of funeral preparations and cremations. 

    • October 21 - November 8: Seattle Restaurant Week. Get a special deal on a three-course meal at 165 participated restaurants. 

Find Dockage in Washington


Inland Waterways



Reserve in the Intracoastal Waterway


The Great Lakes


  • Chicago – 

    • October 6 - 7: The 31st Annual Apple Fest. Dozens of vendors participate in Apple Fest every year, selling everything from candy apples to scarves and hats. 

    • October 7: The Chicago Marathon

    • October 24 - 28: Night of 1,000 Jack-o'-Lanterns. More than 1,000 hand-carved pumpkins, some as large as 150 pounds, will light up the night at the Chicago Botanic Garden. The LED-lit jack-o'-lanterns will be staged along a festive, paved pathway, starting at the Esplanade. 


Reserve in Illinois


  • Detroit – October 13: Detroit Boat Club Beer Fest 2018. Sample 60+ craft beers and enjoy a fall day on the Detroit River at one of Detroit's oldest and most historic buildings. 


  • Port Washington – October 4 & 21: Scuba Diving Local Shipwrecks an Dive sites. 

Find Dockage in The Great Lakes


Reminder: Share your event! Email amanda.jones@dockwa.com or post to our Facebook Group.

Post by Amanda Jones

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