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11/3, 12PM, Holiday Fashion Show for Colorful Kidz, Clancy’s, Dennisport – Want to make sure your holiday look is on point? Treat yourself to a delicious luncheon, signature cocktails, a holiday fashion show, silent auction, and a pop-up holiday boutique – all for your $40 ticket, part of which benefits Colorful Kidz and the work they do transforming and redesigning the bedrooms f ill children on teh Cape. Tables are available. Learn more and reserve your seat here.
11/6 – 11/9, 5th Annual Provincetown Food and Wine Festival – A 4-day celebration of food and drink! Tastings, sip and strolls, dinners, brunches, live music events, dances – you name it – and several prix fixe menus as well. The Grand Tasting happens on Sunday the 8th. Check out the full schedule here and order your tickets for the Grand Tasting here.
11/7 @ 7:30PM & 11/8 @ 3:30PM, Creare Symphonia in Concert: English Masterworks, Church of the Transfiguration, Orleans – Immerse yourself in the rich lyricism and noble spirit of English orchestral music. This program features masterworks by Edward Elgar, Gerald Finzi, and Ralph Vaughan Williams, including Fantasia on a Theme by Thomas Tallis and Fantasia on ‘Greensleeves’, and Elgar’s Elegy, Op. 58. Experience the music that captures the soul of a nation through sweeping melodies, tender reflections, and pastoral grandeur. Tickets: 508-240-2400 | artsempoweringlife.org FREE for students and youth.
11/7, 7PM, A Conversation with Best Selling Author Elin Hildebrand, Hyannis Arts Hall – If you’re a fan of Elin Hildebrand, come hear her speak about her latest novel The Academy – and participate in a Q & A. Doors open at 6:15, beer, wine and beverages will be available for purchase, and Ms. Hildebrand will sign copies of the book after the session. Register here. A portion of the proceeds will benefit Hyannis Arts Hall on Willow Street, a new nonprofit cultural arts center just off Main Street in the East End.
11/8 – 11/12, 13th Annual Field of Honor, Johnny Kelley Park, South Dennis – This annual display of flags, over 400 of them, reminds us of the sacrifices our Veterans have made. Buy a flag to honor the memory of a loved one, thank someone who is currently serving, or honor the service of someone who served with honor. Proceeds go to local organizations that help veterans. After the display, you keep the flag you’ve purchased to fly or keep as a memento.
11/8, 11AM, Grist Mill Grain Fest, Plimoth Patuxet Museum – An outdoor festival that will explain our local grain chain – corn, wheat, and more. You’ll also meet the farmers, millers, bakers, and other partners who grow and make things with grains. More info is here.
11/8, 9 AM, “Boat America” Boat Safety Course, Orleans Police Station, 99 Eldredge Park Way, Orleans – Hanson-Milone Act requires boaters in Mass to obtain a Safe Boating certificate. Those born on or after 1/1/1989 need to get this by April 2026, Those born before that date have until April 2028, but don’t wait! This course satisfies that requirement. Email Nauset Flotilla U.S Coast Guard Auxiliary at [email protected]. Cost is $45.00 for materials, cash or check only. Ages 12 and up, no limit! Click here for more information.
11/8, 12PM, 3rd Annual Oyster and Sushi Festival, Flying Bridge Restaurant, Falmouth – Spend the afternoon enjoying a variety of oysters from farms across the Cape, fresh sushi rolls, and special menu items – along with drink specials like the refreshing Oyster Shooter. Live entertainment with classic Yacht Rock tunes, fun giveaways and lawn games will also be part of the party. Get tickets here.
11/12, 5PM, Taste of Barnstable, Cape Cod Gateway Airport, Hyannis – Get ready for an unforgettable evening celebrating the best of Barnstable’s culinary scene! The Greater Hyannis Chamber of Commerce proudly presents the Taste of Barnstable, where local restaurants and eateries come together for one delicious night of food, flavor, and community spirit. Click here for more information.
11/14, Glassblower’s Christmas Kickoff Celebration, Sandwich Glass Museum – During this annual celebration, festively decorated trees will be displayed throughout the museum with each tree covered in beautifully unique glass ornaments made by local glassblowers. All ornaments will be available for sale through December 30th. To kick off this sale, attend this festive evening featuring the unveiling of the Christmas trees,the opening of a special exhibit of paintings by Dodge Macknight that runs through February, light refreshments, and a presentation by Special Exhibit Curator Julia Blakely. Free and open to the public. Get more information here.
11/15, 10AM, 3rd Annual Holiday Market and Open House, Sotheby’s Int’l Realty, Orleans – Several of your favorite local vendors will help you find the perfect handcrafted gifts you’re looking for at this fun market.
11/19, 3PM & 7PM, The Glenn Miller Orchestra, 204 Sisson Road – In The Mood for swing? Don’t miss the most popular and sought-after big band of all time on their stop on Cape Cod as a part of their 2025 international tour! The world famous Glenn Miller Orchestra will perform their hit songs including In The Mood, Moonlight Serenade, Chattanooga Choo-Choo, Pennsylvania 6-5000, String of Pearls, Tuxedo Junction and more classic songs of the swing era at The 204 auditorium. Click here for more information.
11/19, 8AM, Philanthropy Day 2025, Emerald Resort, Hyannis – Join hundreds of professionals from non-profits across the Cape for a day of learning and recognizing the dedication of people who run and support the many charitable organizations in our area. It’s a celebration of charitable giving and a chance to share best practices in fundraising, with dynamic speakers and a delicious luncheon. Get your tickets here; tables and individual tables are available.
11/21, 7:30PM, The Pilgrims on Cape Cod & the Signing of the Mayflower Compact, Performing Arts Center, Brewster – Presented by G. Thomas Ryan as part of a year long series, God of Our Fathers: The Mighty Miracles of the American Revolution. Info: 508-240-2400 | artsempoweringlife.org FREE
11/21 – 11/23, America’s Hometown Thanksgiving Weekend, Plymouth – A full weekend of celebration in Plymouth, including concerts, food trucks, a craft wine and beer garden, a children’s pavilion, a harvest and crafts festival, and of course the highlight – America’s Hometown Thanksgiving Parade, on Saturday. This is one of the country’s most historically and chronologically accurate parades, and it’s nationally ranked, airing across the US. Channel 5 will be broadcasting live Saturday morning beginning at 10, and there will be a re-broadcast on Thanksgiving morning. Whether you plan on attending in person or viewing remotely, all the info you need about the celebration is here.
11/21 – 12/14, 19th Annual Holidays at Highfield – The Victorian era will be celebrated during the holidays at Highfield Hall and Gardens this year – come experience the charm of The Shopkeeper’s Noel. Enjoy gorgeous themed decorations, festive music, seasonal activities (some of which require a materials fee), and holiday displays that will delight visitors of all ages. Shop the Gift Gallery for handcrafted artisan treasures, or do some creating yourself in the holiday craft room. For available dates and activities, click here.
11/22, 10AM, Eastham Turnip Festival, Town Wide – A celebration in 3 parts – Turn Up for Fun, Turn Up for Tunes, and a Taste of Turnip! Check out all the activities and special restaurant offerings highlighting the world famous Eastham turnip. For a full schedule of events and participating restaurants, click here.
11/26, 3PM, Lighting of the Pilgrim Monument – Celebrate the beginning of the holiday season with this annual Outer Cape tradition. Enjoy a cash bar and a DJ spinning tunes beginning at 3; the lighting happens at 5:15. Details and directions are here.
11/28 & 11/29, 4:30PM, Services of Advent Lessons & Carols, Church of the Transfiguration, Orleans – Embrace the spirit of the season with candlelit services of Advent Lessons and Carols—uplifting readings, prayers, and carols sung by Gloriæ Dei Cantores at the Church of the Transfiguration—a cherished tradition for over thirty years. Doors will open one hour before the service; no tickets required.
