SEPTEMBER 28-OCTOBER 4

Nantucket Restaurant Week is held Monday, September 28, to Sunday, October 4 with more than 35 participating restaurants across the island offering discounted meal prices, new menu options, and more. Participating restaurants offer three-course meals at discounted prices ranging from $35 to $45. In addition, many of the restaurants try out new dishes or other concepts at this time, showcasing their cooking staff’s talents. For more information, visit nantucketrestaurantweek.com.

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OCTOBER 3

Cape Cod Cranberry Day will be held at the Thornton Burgess Society’s Green Briar Nature Center in East Sandwich from 10 a.m. to 4 p.m. on October 3, celebrating this native berry. See cooking demonstrations in the historic 1903 Jam Kitchen using traditional cranberry jam and relish recipes. Enjoy a homemade cranberry dessert, clam chowder, or chili served from 11 a.m. to 2 p.m., or spend some time walking the nature trails. The fee for dessert is $4.00. For more information, visit thorntonburgess.org.

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OCTOBER 6

The Cahoon Museum of American Art in Cotuit is sponsoring a special bus trip on Tuesday, October 6, from 9 a.m. to 5 p.m. to the Old Schwamb Mill, the Jason Russell house, and the Cyrus Dallin Art Museum in Arlington MA. Tickets are $50 for members of the museum; $60 for non-members. For more information, visit cahoonmuseum.org, or call 508-428-7581.

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OCTOBER 9-11

A Friday night cocktail party celebrating the Artists Association of Nantucket’s (AAN) permanent collection kicks off the island’s ever-popular Wet Paint Weekend, a must-go cultural event. On Saturday and Sunday, member artists paint at different spots around the island for visitors to observe. The weekend concludes with a silent auction and a benefit dinner at elegant Le Languedoc restaurant at 24 Broad Street on the island. For information, visit nantucketarts.org.

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OCTOBER 10

Pumpkin Day at Bourne Farm is a fun event on Saturday, October 10, from 9 a.m. to 3 p.m. at this beautiful farm in North Falmouth featuring hayrides, face painting, a bounce house, a petting zoo, crafts, and a pick-your-own pumpkin patch. Admission and parking is free. Lunch options are available and a bake sale will be held. For information, visit saltpond.info.

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OCTOBER 10-12

The three-day Yarmouth Seaside Festival, held Saturday to Monday, October 10-12, features an abundance of fun activities. The lineup includes pie-eating contests, kayak and canoe races, a road race, pumpkin decorating, clown shows, live music, a large parade, and much more. Most of the activities will be held at the Laurence MacArthur Elementary School at 1175 Route 28 in Yarmouth, however additional events will take place around town. The seaside festival is free and open to all—Yarmouth residents and visitors. For more information, visit yarmouthseasidefestival.com, or call 508-778-1008.

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OCTOBER 15-18

Every October, Martha’s Vineyard hosts a great gastronomical highlight: the Martha’s Vineyard Food and Wine Festival. Those who make their way to the event can sip wines from around the world, enjoy gourmet dinners, and savor aged cheese from the Edgartown shop Black Sheep. The festival runs from Thursday through Sunday, October 15-18, and events are held at various venues on the island. For ticket information and a full schedule of events, visit mvfoodandwine.com.

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OCTOBER 17

Don’t miss the chance to purchase “seconds” pots created by local potters, which may be beautifully flawed. This event is held Saturday, October 17, from 10 a.m. to noon at the Cultural Center of Cape Cod. These “seconds” are pots that may have imperfections—and therefore sell for less—but are still beautiful! Come hunt for bargains, handmade by local artisans. The annual sale is a major fundraiser for the Cape Cod Potters, with proceeds benefitting scholarships and covering financial hardships for some locals in need. For more information, visit cultural-center.org

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OCTOBER 24

Head to the Sandwich Glass Museum’s 3rd Annual “PumpkinFest,” held Saturday from 10 a.m. to 2 p.m. The day’s festivities include one-of-a-kind pumpkins and a pumpkin patch filled with hand-blown glass pumpkins. Enjoy delicious homemade baked goods available for purchase. All event proceeds benefit the Sandwich Historical Society and the Sandwich Glass Museum. This event is free and open to the public. For more information, visit sandwichglassmuseum.org, or call 508-888-0251.

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OCTOBER 24

View the creative displays of “Pumpkin People in the Park” at Kate Gould Park in Chatham during the 5th annual Oktoberfest on Saturday, October 24, from noon to 4 p.m. The massive pumpkin creations are seen on Main Street in Chatham and the surrounding area, including Kate Gould Park. Attendees can enjoy live music, a cupcake and pie contest, bobbing for apples, and much more. For more information, visit oktoberfestinchatham.com, or call 508-945-3395.

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NOVEMBER 14-DECEMBER 30

Festive holidays in Sandwich begin at the Sandwich Glass Museum on Saturday, November 14 through December 30, when the museum presents its Glassblowers’ Christmas. Hundreds of unique glass ornaments made by fine local and national glass artists adorn Christmas trees in the contemporary gallery. The museum’s Open House will be on Saturday, December 5 from 9:30 a.m. to 5:00 pm and includes a “Mystery Discount” and refreshments. The decorations on the glassblowers’ trees are available for purchase as well as an array of glass objects on display in the museum store. For more information, go to sandwichglassmuseum.org.

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NOVEMBER 25

The Pilgrim Monument has been one of the Cape’s most iconic structures since its construction was completed in 1907. With the holiday season around the corner, watch the Provincetown night sky become illuminated as the 252-foot monument is transformed into a shimmering gem on the skyline. The “Annual Lighting Ceremony” to commemorate the Pilgrim’s first landing in America is held November 25, from 5 to 7 p.m. This year, Provincetown’s children will be honored. For more information, visit pilgrim-monument.org, or call 508-487-1310.

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NOVEMBER 27, NOVEMBER 30, DECEMBER 4,

Circle these dates on your holiday calendar for a festive time featuring holiday decorations and handmade gifts from Falmouth’s Highfield Hall’s elegant gift gallery, visits from Santa, and more. The festivities are held from 10 a.m. to 4 p.m. For more information, visit highfieldhallandgardens.org.

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NOVEMBER 28-29, DECEMBER 5-6, 12-13, 20-21

Come to the Green Briar Nature Center’s Country Christmas Open House during Christmas weekend in East Sandwich. Taste a sampling of delicious Jam Kitchen products and enjoy a cup of mulled cider. Browse among a variety of holiday gifts in the Green Briar shop offering jams, jellies, relishes, books, an abundance of nature-related items as well as books, games, puppets, and toys for children. Unique handmade gifts and home decorations created by Green Briar Crafters will also be available. For information, visit thorntonburgess.org.

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DECEMBER 6-7, 13-14, 20-21

Enjoy holiday favorites including apple cider during “Country Christmas” at Green Briar Nature Center and Jam Kitchen at 6 Discovery Hill Road in East Sandwich. Marvel at holiday decorations inspired by an old-fashioned country home, and pick up last minute Christmas and holiday gifts like jams and jellies at the Green Briar Shop. The event runs on Saturdays (December 6, 13, and 20) from 10 a.m. to 4 p.m., and Sundays (December 7, 14, and 21) from 1-4 p.m. Visit thorntonburgess.org for more information.

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DECEMBER 12

Put on your best holiday attire and head to Highfield Hall & Gardens in Falmouth for the annual Highfield Hall Holiday Ball. More details on this ever popular event coming soon—visit highfieldhallandgardens.org.