Here's our round-up of some of the best food & drink festivals on Cape Cod, in every season!

Sample the area’s best chili and then vote for your favorites at the annual Awesome Chili Challenge (April 22, 2023), held under the heated tent at the oceanfront Popponesset Inn. Dancing to the sounds of the Grab Brothers Band also helps kick up the heat at this 21+ event! Each bite counts, as the event benefits the Boys & Girls Club of Cape Cod. More info>

Sample exquisite wines and savory bites at the Nantucket Wine & Food Festival (May 17-21, 2023). What began in 1996 as a one-day wine tasting has grown over the years to encompass five days of tastings, dinners, cooking demonstrations and seminars. Meet and mingle with winemakers and award-winning chefs from around the world! More info>

Wellfleet Restaurant Week (May 31-June 6, 2023) shines a light on the town’s well-deserved reputation for freshly caught seafood and delicious cuisine. Bring your appetite; the week-long promotion showcases prix-fixe menus and dining specials at such popular local eateries as Van Rensselaer’s Restaurant & Raw Bar, PB Boulangerie, Moby Dick’s Restaurant and the Wellfleet Bookstore & Restaurant. More info>

Baklava, spanakopita, and dolmades make up just some of the authentic Greek cuisine waiting to be sampled at the St. George Greek Orthodox Church's annual Greek Festival, held every July on the church grounds in Centerville. Nosh on a feast for the senses, while enjoying Greek music, dancing and traditions. More info>

The wildly popular Cape Cod Food Truck and Craft Beer Festival barrels into the Cape Cod Fairgrounds in East Falmouth every summer (August 5, 2023). More than 30 food trucks from all over New England are on hand to serve up their best bites. Try everything from spicy Korean treats that melt in your mouth to traditional BBQ and wood-fired pizza. There’s also a beer tent, live music and a craft market to keep you entertained once you’ve satisfied your appetite.

Another summer highlight occurs when a section of Steeple Street in the Mashpee Commons is transformed into “Little Italy” for a one-night celebration of Italian cuisine and culture at the Mashpee Chamber’s annual La Tavola (August 4, 2023). Three hundred people gather for a five-course Italian feast with wine, while being serenaded by an Italian Tenor. It’s deliciously festive and fun. More info>

The Cape Cod Brew Festival in September celebrates everything we love about American craft beer. Held at the Cape Cod Fairgrounds in East Falmouth, the fest features over 50 breweries and 150+ styles of beer for your sipping pleasure; food vendors are also on hand. More info>

Take a bite out of Sandwich (literally) at the annual SandwichFest (October 7, 2023). Sample from food trucks and restaurants, while you peruse local vendors, craftsmen and artists set up at Hoxie House and along Water Street in Sandwich. A beer & wine garden provides festive libations, and kids’ activities include face painting and lawn games. More info>

Every autumn, Mashpee Oktoberfest takes over the Village Green in Mashpee Commons for a day of merry-making. The celebration, put on by the Mashpee Recreation Department, includes an authentic German Bier Garten, food vendors with German cuisine, over 50 crafters, carnival style games, pumpkin decorating, stein races and entertainment. More info>

Next up is the Chatham Oktoberfest (October 21, 2023) at Kate Gould Park in Chatham, where you can nibble on bratwurst while sipping on local beer. There is live entertainment, craft booths and the extremely popular “Pumpkin People in the Park” displays, created by local businesses and organizations. More info>

A bivalve takes center stage at the Wellfleet Oyster Fest (October 14-15, 2023). What began as a small town celebration has turned into a two-day extravaganza that draws big crowds for shucking contests, cooking demonstrations, local cuisine, a fine arts and crafts fair and a 5K road race. More info>

If you’ve never sampled one of the world-famous Eastham turnips, you can celebrate them in all their glory at the town’s Taste of Turnip Day in November! Local food establishments feature a turnip dish on their menu for one day only (specialties range from turnip soup and turnip side dishes to turnip entrees and even turnip ice cream)! More info>

Last, but certainly not least, Valentine’s Day enthusiasts will love the perfectly timed Osterville Chocolate Fest in February. Past events have included a chocolate dessert contest, dog parade, chocolate manicures, book signings, family scavenger hunts and chocolate-themed promotions in local shops. A surefire way to sweeten the winter season! More info>