Check in weekly for our updated list of events happening on Cape Cod, Nantucket, and Martha’s Vineyard. From concerts and festivals to lectures and community gatherings.
5/5 – 10/6, Eastham Painters Guild for Plein Air Painting – Members of the Eastham Painters Guild plein air paint weekly, 8 – 10:30am, on Tuesday mornings starting May 5 through October 6. All ages and ability levels are welcome to come paint with us! Click here for more information.
10/2 @ 7:30PM & 10/3 @ 3:30PM, America 250 Fall Band Concert: Pursuit of Happiness, Performing Arts Center, Brewster – Come celebrate the American Dream and the Pursuit of Happiness! Music by John Williams, Rogers & Hammerstein, and Leonard Bernstein showcases the energy, ingenuity, and verve that makes our nation bustle and thrive! Info: 508-240-2400 | artsempoweringlife.org (Free for Students and youth 18 & under).
10/3, Sandwich Fest, Water Street, Sandwich – A day to celebrate the very best of Sandwich! Come enjoy a huge arts and crafts show with more than 80 artisans, music, a beer and wine garden, food trucks, and a dog parade! Details are here.
10/3, 2PM, Witches On the Water 2026 Paddle for Family Table Collaborative, 80 Stage Harbor Road, Chatham – Calling all magical paddlers!! Come dressed in your finest Witch regalia (or whatever magical character you choose to be), bring your own SUP (or kayak or paddle boat or any other self-powered aquatic vehicle). This is not a race, just a fun floating parade! All paddlers must register to join us. $50 registration fee per each magical paddler. This amount supports the Witches in holding the event. Each registered participant is required to raise a minimum of $250 which will benefit Family Table Collaborative. This can be from yourself or by inspiring others to donate. It is easier to pay online, but if donors prefer to pay by check, please make all checks payable to Witches On the Water, Inc. Click here for more information.
10/9 @ 7:30PM & 10/10 @ 3:30PM, Reflections: The Waters of Life with Chara Percussion, Performing Arts Center, Brewster – Chara offers joy as a fresh musical voice with the fierce beauty, energy, and synergy of percussion ensemble. Reflections considers the many moods of water—from the quiet serenity of still waters to the force of rushing rapids—and includes the impressionistic music of Maurice Ravel and Claude Debussy and contemporary voices Philip Glass, Owen Clayton Condon, and Rodrigo y Gabriela. At its heart is Pavel Karmanov’s Past Perfect, exploring the tension between pain and beauty, turbulence and stillness. Info: 508-240-2400 | artsempoweringlife.org (Free for Students and youth 18 & under).
10/10, 10AM, Cranberry Harvest Festival, Museums at Aptucxet – A vendor festival and family day dedicated to the cranberry! Enjoy kids’ activities, cranberry-themed story walks along the museum trails, food from the grill, and explore the museums – plus do a little Fall shopping. Hosted by the Bourne Historical Society. Details and directions are here.
10/10 & 10/11, By the Bay Columbus Day Arts and Crafts Fest, Drummer Boy Park – Dozens of crafters to help you get started on your holiday gift selections and more! Click here for vendors.
10/10 & 10/11, 15th Annual Pumpkin Fest, Sandwich Glass Museum – Stop by the Sandwich Glass Museum to browse gorgeous handblown glass pumpkins in every color and style imaginable – along with other fall and Halloween themed pieces – all created by local and regional studio glass artists. The fest will be held rain or shine (there’s a tent), and admission is free – although admission to the museum is ticketed. More info is here.
10/10 – 10/12, Yarmouth Seaside Festival, Joshua Sears Memorial Field and around town – This year the Festival celebrates the 250th birthday of the US! Come be a part of this annual Fall tradition that includes a massive arts & crafts fest, lots of live entertainment, tons of kids’ activities (including pumpkin decorating), the Kooks and Spooks Parade, a big Saturday night bonfire out on Smuggler’s Beach, and Sunday night Fireworks. Get the full schedule of events here.
10/10, 10AM, Fall Festival, Taylor Bray Farms, Yarmouthport – Bring the family to experience the vest that Fall has to offer! Hay-wagon rides, games, pumpkins, hot dogs, apple cider, cider donut holes and more – including a visit with the farm animals! Miniature donkeys, Nubian goats, a Scottish Highland cow and plenty of sheep and chickens call Taylor Bray Farms home. Free to attend, and if it rains, the festival will happen Sunday, 10/11. If you need directions, click here.
10/10, 11AM, Outermost Roots and Blues Fest, Nauset Beach – The last outdoor concert of the season! It’s a celebration of roots, blues, Americana, and folk music, combining national and local artists for an amazing experience, all in support of the Friends of Nauset Beach. Food and drinks will be available. Rain or shine, parking is free (there will be shuttles as well) – please, no pets or outside food or drink. This year’s lineup includes Digable planets, the Grateful Dub, and local favorites G. Love and Special Sauce. Get the full lineup and tickets here.
10/11, 11AM – 2PM or 2PM – 5PM, Fall Frolic, Chatham Bars Inn Farm – Bring the family for live music, lawn games and kids activities that celebrate Fall! Pick your own pumpkin from the farm stand, grab lunch from the Chatham Bars Inn Food Truck, and enjoy beer and wine as well as fresh cider donuts and more — all available for purchase. Admission is $10 per vehicle, and all proceeds benefit local youth sports teams. Rain date is Monday, 10/12. Get your tickets here.
10/14, 5:30PM, Power of the Purse, Wed, Hyannisport Club – This annual fundraiser for the Cape & Islands Way not only celebrates unity, empowerment, and community impact but it gives you the chance to bid on – and possibly go home with – a coveted high-end designer bag, knowing your winning bid will do so much good in our community. Guests will also enjoy delicious food, seasonal cocktails, and meet the 2026 Woman of Impact and winner of the Community Spirit Award. This event ALWAYS sells out – don’t miss out on your chance to be there. Get your tickets here.
10/15, 7PM, Women Rock!, Tilden Arts Center – Hot off their sellout show at the Melody Tent in September, and in partnership with CCftA, these talented Cape performers rock the house with hits from your favorite female artists – like Janis Joplin, Heart, Pat Benatar, Taylor Swift, Adele, and Billie Eilish. Don’t miss it! For the lineup and to purchase tickets, click here.
10/17 & 10/18, Wellfleet OysterFest, Main Street – It’s a two day party in the Fleet – and it’s all about those world famous oysters… and community. Truly, there’s something for everyone to enjoy – great food, dozens of artisan vendors, educational lectures, culinary programs, kids’ activities, live music, a 5K, and of course – the annual Oyster Shuck-Off competition. Admission is ticketed ONLY – and you have to get your tickets in advance. Do that here.
10/17, 10AM, 16th Annual Feet For Flippers 5K, Buzzards Bay Rec Area – Come race for our friends at the National Marine Life Center – virtually or in person! All funds raised will go toward the care of endangered sea turtles and sick or injured seals. Prizes at the finish! Register here.
10/17 @ 7:30PM & 10/18 @ 3:30PM, Creare Symphonia in Concert, Performing Arts Center, Brewster – Join us for Vaughan Williams iconically beautiful The Lark Ascending and Finzi’s music for Shakespeare’s Love’s Labours Lost. Bask in the autumn glow of the 20th century English musical landscape. Info: 508-240-2400 | artsempoweringlife.org (Free for Students and youth 18 & under).
10/21, 5:30PM, Taste of Dennis, Pelham House Resort – The best caterers and restaurants will be proudly serving up their best at this annual food lover’s night out! Live music, a silent auction, and a cash bar will also be part of your evening – and the fun will happen on both floors of this gorgeous venue. A fun, casual, delicious night! Get your tickets here.
10/24, 7:30PM, Sō Percussion Concert, Performing Arts Center, Brewster – Grammy-winning percussion quartet Sō Percussion presents an “exhilarating blend of precision and anarchy, rigor and bedlam” (The New Yorker), fueled by a belief in the unifying power of music. Come experience the joy as they perform music by Steve Reich, Oliver Tarpaga and Kendall Williams! Info: 508-240-2400 | artsempoweringlife.org (Free for Students and youth 18 & under)
10/31, 1PM, Fall Festival, Cahoon Museum of American Art – The perfect way to spend a Saturday afternoon before you go trick or treating! Enjoy some hands-on, fall-themed arts and crafts for all ages, sweet treats, and make a special craft you’ll take home – all while enjoying the current exhibitions. This is a ticketed event, free for members. Get your tickets here.
November thru December, Holiday Events, Chatham Bars Inn – Celebrate the magic of the holiday season at Chatham Bars Inn. From festive traditions and family-friendly activities to seasonal dining, live entertainment, and creative experiences, there’s something for everyone to enjoy throughout the holiday season. Gather with loved ones and make lasting memories by the sea. Click here to see the schedule.
11/6, 7:30PM, Daniel Roth in Concert on the St. Cecilia Organ, Church of the Transfiguration, Orleans – Daniel Roth is Titular Organist at St. Sulpice in Paris. Don’t miss his return performance to Cape Cod this fall! From his last concert in Orleans: “Roth certainly opened our ears with a sonic coloring book of organ effects infused with the incense and visual feast of a great cathedral. The master improvisor thus sent us off with a fitting, deeply considered, and not-to-be forgotten postlude.” -Boston Musical Intelligencer “Daniel Roth showed himself a master both stylistically and technically …”—Musical Times. Info: 508-240-2400 | artsempoweringlife.org (Free for Students and youth 18 & under)
