Photo: John Ashton

October on Martha's Vineyard is often summer-like, with warm sunny days, cool evenings and serenity. Fall colors illuminate landscapes along hiking trails like Menemsha Hills, plus both Cape Poge and Mytoi on Chappaquiddick, among others. Crowds thin, more room for everyone; hotels and inns offer shoulder-season rates (easier on budgets), autumn restaurant menus entice locals and visitors. Events include Gay Head Road Race and Golf Fore Kids (both 10/6), Vineyard Artisans Fall Festival (10/12), Cranberry Day, 21st Annual Artisans Festival (10/12-10/13, 10 am to 4 pm); Women in Film Festival (10/18-10/20); Morning Glory Farm’s Pumpkin Festival (10/19); MV Ag Society Harvest Fest (10/20); OB Halloween (10/26) and VH Halloween (10/31). Visitors can bike, shop, kayak, beach, museums, golf, sightsee and just relax! It’s all near and it’s all HERE!

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As the season turns to fall color in the Mohawk Trail Region there is much to do! Take one of the famous 5 Driving Tours for great foliage views. Check out some of the fall festivals: 68th Annual Fall Foliage Parade, Ashfield Fall Festival, Crafts of Colrain, 60th Annual Festival of the Hills, 26th North Quabbin Garlic & Arts Festival , RambleFest & Mount Greylock Ramble and 36th Old Deerfield Holiday Sample!

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Scary, Spooky season is here! Check out Goodnow Farms Haunted Barn Party 10/19, Halloween Hullabaloo at Discovery Museum 10/26 & 10/27, and The Haunt, A Wedding in Deadwoodville at HCA 10/18-20 and 10/25-27. Dive deep into fall at Applefest Family Day 10/6 at Wayside Inn, Ashland FallFest 10/19, Craftacular Beer & Spirits Tasting 10/27 in Natick, and the Flow into Fall Retreat hosted by Synergy Wellness 10/27. See website for even more exciting MetroWest events!

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Photo: Michael Galvin

Nantucket’s October offers sunny days, cool nights ideal for family, friends’ or couples’ getaways. Restaurant Week  (10/1-10/6) returns and Cobblestones & Cranberries (10/11-10/14) offers shoppers’ prizes. Fall Fashion Show (10/12) and Nantucket Half-Marathon (10/13) are reasons for extended long weekend getaways. Nantucket Shorts Festival (10/13), Trunk or Treat (10/20 1 to 4 pm) and A Nantucket Halloween round-out October. Fall colors illuminate hiking/biking trails providing heady inspiration for en plein air, photography or for its majestic beauty. Visit Nantucket Whaling Museum, Cultural District and shop Main Street stores, galleries and boutiques. Spend a night/weekend in a lovely inn or hotel at quiet season rates, explore, stroll, bike or kayak. 

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Photo: John Andrews Photography

Enjoy eleven days of agriculture, entertainment, and great food at The Topsfield Fair October 4–October 14. Haunted Happenings is the largest celebration of Halloween in the world! Visit Salem for the parties, parades, vendor fairs, walking tours, museums, attractions, and special offers. Plan your trip, put on your costume, and join in a month that is steeped in history, haunts, and a bit of magic. There is something for everyone!

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Stroll the darker side of Plymouth history along haunted streets in search of ghosts, orbs, phantom sounds and anomalous EMF readings with the Spirit of Plymouth Haunted History Tours. Times and days vary. On October 11-27, Company Theatre presents “What Ever Happened to Baby Jane.” Twisted memories lurk in the decaying mansion where aged child star, Jane, now a recluse, lives with her invalid sister as she attempts to resurrect her career. Purchase tickets here. And New England Cranberry Festival at Edaville Family Theme Park offers steam train rides, flea & craft market, amusement rides, and more!



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Trolleyoke Tuesday – October Edition is October 8! Join Viva Fall River for karaoke on-board the Fall River Trolley. During October weekends at Simcock Farm, pick your own pumpkins, take a hayride or stroll through the corn maze. The 19th Annual Blount Fine Foods New Bedford Seaport Chowder Festival will take place on October 12 at the Pier, with local restaurants and caterers competing for your vote! Battleship Cove Boo Bash Trick-or-treat aboard the historic naval vessels at Battleship Cove happens October 25-26. Meet friendly costumed characters as you tour the museum!  

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While it’s always bittersweet to see the summer end, our hope is that the warm weather will continue right into the fall, when the Berkshires becomes a magical palette of crimson, orange, and yellow. Make this the year you come for the foliage, and experience the excitement of the 68th Annual Fall Foliage Parade in North Adams! This year’s theme is "Berk du Soleil - The Greatest Show in North Berkshire", a fun take on the popular Cirque du Soleil, and we are pulling out all the stops. The Parade will be held Sunday, October 6 at 1 pm, featuring floats, bands, and marching units from across Berkshire County!

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The 36th Annual Lowell Celebrates Kerouac! Festival will be held October 10-14! Poetry, musical performances, tours and more are planned to commemorate the life and legacy of Jack Kerouac for the LCK Festival. Jack Kerouac was born in Lowell and became a writer there. Each October, the Lowell Celebrates Kerouac! (LCK!) Festival illuminates his local influences and explores his enduring impact on music, art, and literature.

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Fall is in full display at Central MA's new Harvest Festival in Worcester, Sturbridge's 34th Annual Harvest Fest, and the Fall Festival at Stowe Farm. Enjoy spooky season theatrics at Phantoms by Firelight at Old Sturbridge Village, and at JMAC where The Hanover Theatre Repertory presents The Crucible. There is a weekend long BACHtoberfest at Mechanics Hall present by Music Worcester, and Worcester’s DCU Center hosts Worcester Railers hockey, Hot Wheels and Disney on Ice.

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The Ashfield Fall Festival returns on October 12 -13 from 10 am to 5 pm! Nestled in the hills of Western MA, this charming annual event features handmade crafts from jewelers, woodworkers, painters, and more. Indulge in seasonal treats like fresh pumpkin donuts, maple sno-cones, and hearty eats, including chili and chicken pot pie. The kid-designed midway offers fun games for all ages. Celebrate autumn with local food, art, and entertainment in beautiful Ashfield! Learn more here.

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Beginning October 17, for the first time ever in Boston, visitors can experience the wonder and tragedy of the world’s most legendary ocean liner at TITANIC: The Artifact Exhibition. Spanning more than 15,000 square feet, the exhibit will feature nearly 250 authentic artifacts from the 1912 shipwreck, meticulous recreations of the ship’s interior and exterior, replicas of famous rooms and the legendary Grand Staircase, plus much more. For details, visit titanicboston.us.

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Autumn is festival season on Cape Cod! On Sunday, Oct. 6, gather around the vines of Truro Vineyards for a day of American Roots Music at the Vinegrass Music Festival. Arts and crafts, rides, fireworks and live music take center stage at the Yarmouth Seaside Festival on Oct. 12-14, while seafood is the headliner at Wellfleet Oyster Fest October 19-20. From Oct. 14-31, stroll through downtown Chatham to admire the fascinating pumpkin displays at Pumpkin People in the Park. And on Saturday, Oct. 19, enjoy vendors, live music, German food and an authentic Bier Garten at Chatham Oktoberfest. (also save the date for the Mashpee Oktoberfest Oct. 5!) Explore more about Fall on Cape Cod here!

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Visit the birthplace of basketball October 13th to see the best in the game take their rightful place in the Naismith Basketball Hall of Fame! Springfield is where the game was invented and the one and only location in the world where you can see artifacts detaining the history of the sport with state-of-the-art interactive displays. Plus if you visit during Enshrinement Weekend, you’ll be on hand to witness the live televised 2024 Enshrinement Ceremony attended by over 40 returning Hall of Famers. Make it a Western Mass weekend and visit Six Flags New England Frightfest, the Springfield Museums and MGM Springfield.

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Photo: Lynne Graves

An autumn tradition returns! The Paradise City Arts Festival showcases handcrafted treasures over a three-day weekend in Northampton. Discover more one-of-a-kind creations at Easthampton’s Art in The Orchard, where a half-mile sculpture trail winds its way through a working apple orchard (pick a bushel of your favorites as you stroll!). See nature’s artistry in the spectacular foliage viewed from The Summit House, atop Mt. Holyoke in Skinner State Park, and in dinosaur tracks at the Beneski Museum of Natural History. Wonder abounds in Hampshire County!

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You don’t have to be a skier—or even love snow—to head to enjoy the festivities at Wachusett Mountain Ski Area this month! Fans of authentic German beers and local craft brews will gather on October 5 & 6 for a German folk festival with a New England accent. The Oktoberfest features stein hoisting, keg toss contests, music, food and skyrides. The focus turns to apples the weekends of October 19 and 26, with “everything apple” on the menu, along with crafters, music, contests and skyrides!

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