October Events from Cape Cod to Boston

October is here and Fall is in full swing! Bring on the pumpkin picking, layered looks, and home décor transition! In New England, we celebrate the new season with a slew of events and activities from Boston to Fall River and from Wareham to Provincetown. No matter where you are in Eastern Massachusetts – we wanted to give you the pick of the line from light and fun day trips to some seriously spooky night events:

We are kicking it off with the Cape:

Mashpee’s Annual Octoberfest

October 2nd from 10am-4pm at the Mashpee Commons

With over 50 crafters, carnival-style games, pumpkin decorating, great food, and an authentic German Bier Garten there will be something that everyone in your family can enjoy! Visit the Mashpee Commons on October 2nd to start off the month right!

Barnstable Village Haunted & History Walking Tours

Open Daily, Register at the US Coastguards Heritage Museum

Interested in the spooky history of the Cape? Walk the historic and haunted “Old Kings Highway” in Barnstable Village. The walk will include over 10 stops, each with its own haunting stories of the past, which will leave you with some new historic knowledge and some goosebumps!

Wellfleet’s Pumpkin Palooza

October 31, after 3pm on Mainstreet in Wellfleet

Get your pumpkin carving sets ready and get carving. Bring your fall masterpiece to the Wellfleet Preservation Hall where they will put them on display for all to see. Costumes are encouraged and treats will be provided for those who participate!

Chatham’s Pumpkin People in the Park

October 15th– October 31st in Kate Gould Park and the Bandstand on Main Street

Chatham has been known for its passion for the Halloween season. Do you know what they are also known for? The Pumpkin People in the Park! The local businesses put their creativity to the test as they design seasonal displays involving pumpkins.

Next up, South Coast:

South Coast Soiree

October 1st , 5:30pm-8pm at the ‘My Brother’s Keeper’ Dartmouth Facility

Celebrate the new season outdoors with friends, food, live music benefiting the My Brother’s Keeper food assistance program supporting more than 7,200 families in need.

New Bedford Octoberfest

October 2nd, 3pm-12am at the Pier 3

The South Coast Business Alliance presents the 15th annual New Bedford Oktoberfest. Enjoy great food and drinks from local vendors and food trucks while you listen to the live entertainment! Ticket proceeds go to support at-risk youth and education-based charities.

Fairhaven Kids Fest

October 9th 10am-3pm

The first annual Fairhaven Kids Fest is almost here! Enjoy Fall-themed children’s arts and crafts, local vendors, good food and live entertainment will be there for the whole family to enjoy!

Lizzie Borden House Ghost Tours 

Open Daily, 7pm-9pm in Fall River

Suchuck’s corn maze is your one-stop shop for all things family, farm, and Fall fun! Find your way through the corn maze, pick your perfect pumpkin, visit the petting zoo and enjoy a hayride with your family all in one place!

 And now the Spooky South Shore:

Spooky Sips

October 28th,  virtual hosted by The Wine Cellar Outlet Walpole

What is better than a wine tasting? A spooky Halloween tasting paired with a costume contest, candy, and more! Save the date for the Spooky Sips event sponsored by the Wine Cellar Outlet!

Sauchuk’s Corn Maze & Pumpkin Patch

Open Daily, 200 Center Street Plympton, MA

Suchuck’s corn maze is your one-stop shop for all things family, farm, and Fall fun! Find your way through the corn maze, pick your perfect pumpkin, visit the petting zoo and enjoy a hayride with your family all in one place!

Weymouth Farmer’s Market

October 3rd, 10am -1pm at Weymouth High School

Join the Weymouth community for their last farmer’s market of the season! The Weymouth Farmers market allows for public engagement by creating a place where residents, farmers, and producers can connect and share with the community.

Halloween On Main Street

October 29th, 3pm-5pm at the Plymouth Memorial Hall

Enjoy a trick-or-treating stroll on main-street Plymouth! With over 65 participating local merchants there will be plenty of Fall fun for your family and friends.

And of course, we can’t forget Greater Boston:

Harpoon Dogtoberfest

October 3rd, 10:30am-4pm, at the Harpoon Brewery

If you love dogs and the Fall season, this is the event for you!  Enjoy a one-mile fun run (or walk) with your furry friend then make your way to the “barking lot” party for Harpoon beer, food trucks, and music!

Sinners and Saints Haunted Halloween Cruise

October 29th, 7pm-9:30pm boarding at Provincetown II Boat

Start off Halloweekend with a night at sea during Boston’s biggest Haunted cruise. Enjoy a night of drinks, ghoulish grub, music and a costume contest! Event is 21+.

2021 Hawthorne Hotel Ball

October 23rd, 7:30pm-11:30pm

The Hawthorne Hotel is known for its elegance and historic presence in downtown Salem. Enjoy a night of frights, refreshments, music, entertainment and so much more.

Old Town Trolly’s Ghosts and Gravestones Tour

Open Nightly, boarding at the Boston Marriott Long Wharf

The Boston Trolleys are a staple way to tour the city and see all the sites it has to offer. With Boston’s unique and lengthy history, you know it is bound to have some spooky stories to share. Sign up for a late-night tour of the city that is accompanied by haunting historic tales.