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Autumn on Cape Cod

There are still many things to do and see on Cape Cod in autumn. With less tourists and less hot and humid weather, Cape Cod becomes the perfect location for a great getaway! Check out our list of ways to enjoy Cape Cod in the fall.



Barnstable Village’s Haunted & History Tour


Held Sun, Tues, Wed, Thur & Sat at 7 p.m. until November 15, 2022. Host Derek Bartlett will bring you down The King’s Road and stop at locations such as The Superior Court House, The Hedge House, Cobb’s Hill Cemetery and then you will GO INTO The Oldest Wooden Jail in America (photo above) that is actively haunted and many more locations. There are over 6 children entities that haunt locations throughout Barnstable village. For more information, click here.

Barnstable Village’s Ghost Hunters Tour

Held Friday & Monday at 7 p.m. until November 15, 2022. Join founder, Derek Bartlett, as your tour guide. He will bring you down The King’s Highway and stop at locations such as The Barnstable House that has a nickname The House of 11 Ghosts, The Hedge House and many, many more locations. You will enter Cobb’s Hill Cemetery and listen to the stories and then be handed a digital voice recorder and he will teach you how to collect EVP’s (Electronic Voice Phenomenon/voices of the dead) where you then will walk the cemetery to try to capture evidence yourself. You will then be brought into The Oldest Wooden Jail in America, that is actively haunted. The village has over 6 children entities that haunt locations throughout the 3 hour tour and about a 1 mile walk. For more information, click here.



Looking for the perfect spot to grab a cold beer? Local craft beer can be found from Bourne to Provincetown, many with taprooms to sample the offerings. Some locations have both indoor and outdoor seating with light food offerings. Click here for a list of the 15 best local breweries on the Cape.



The tenth annual Cape Cod Brew Fest is scheduled for Saturday, September 24, 2022 at the Cape Cod Fairgrounds. Join for a celebration of American craft brewers and sample from 60+ breweries and over 150 styles of beer. The event will have one session from 2:00 – 5:30 p.m. All beverage samples are included in your ticket, access to food vendors and much more. Every attendee will receive a custom glass as they exit the festival. The Cape Cod Brew Fest is a private, ticketed, 21+ event. No one without a ticket or under the legal age will be admitted, including minors, children, infants and babies. For more information, click here.


Get Outside & Hit the Hiking Trails

There’s no time like the present to get outside and explore the special places Barnstable has to offer. The Barnstable Land Trust publishes a Trail Guide representing 34 locations and almost 95 hiking trail miles in the Town of Barnstable. In addition, the Cape Cod Pathways Trail Guide showcases 21 miles of trails, including spurs, that stretch across the Barnstable section of the multitown Pathways trail network. For for a detailed list of locations and to access the guides, click here.


Words in the Wild Hiking Trails

Launched by Barnstable Land Trust (BLT), Words in the Wild, is a unique hiking trail initiative that features four original site-specific poems penned by local poets. Each poem has been etched onto individual cedar trail signs that include a QR code connecting to audio recordings and other information. For more information on how to access this trail, click here.



As one of Yarmouth’s biggest attractions, this sand sculpture trail in 2022 features 32 family-friendly sand sculptures which change annually. The trail will be available for viewing from Memorial Day until mid-October. Download the Sculpture Trail map and as you explore the Cape, take selfies to post on Facebook or Instagram or share with friends and family. Just be sure not to get to close or touch the sand sculptures! For more information, click here.



Fall is a great season for golf on Cape Cod. The heat of summer has passed, and many courses are enjoying some of their best playing conditions of the year. Since it is no longer peak season, the rates for green fees, cart rentals and more usually drop in the fall. The courses are in good condition and the competition for tee times is nowhere near as intense as during the summer months. From Bourne to Truro, a wide variety of layouts are offered on 27 public courses that never fail to please and most courses on the Cape stay open all winter. You can access a list of public and private Golf Courses by clicking here.



Cape Cod’s beloved OysterFest is returning LIVE in 2022! Kicking off September 19, 2022 and concluding October 16, 2022, come celebrate with fun, tasty, and educational pop ups for all to enjoy. Shellfish and Wellfleet have long been intertwined. Enjoyed by native Pononakanet and later European settlers, commercial sales began in 1665. Wellfleet oysters are internationally renowned for their superlative flavor. Wellfleet’s centuries old shellfishing tradition continues to this day. Wild harvesters and shellfish farmers generate nearly $8 million in sales annually which is 25% of the state’s seafood landings! Click here to access a list of events.


Art & Oyster Crawl 2022

There will be 3 Art & Oyster Crawls this year to celebrate two of Wellfleet’s treasures: outstanding art galleries and delicious shellfish. The Art and Oyster Crawls will be held on September 24, October 1, and October 8, 2022. You will receive an evening overview, be given a gallery guide and a SPAT cup for drinks. Then you can visit with all or some of the participating galleries. Enjoy freshly shucked Wellfleets™, the quintessential American Oyster ™ and other food paired with fine wines, craft beer and nonalcoholic drinks as you take in Wellfleet’s art scene. Meet and talk to the shellfishermen and women who bring us the amazing Wellfleet oysters and clams. The event runs from 4:30 – 7:00 p.m. and will be held rain or shine. Sunset is at 6:08 p.m. and the streets are dimly lit so bring a flashlight! Participating galleries include Newcomb Hollow Shop & Gallery, AMZ Gallery, Marrinan Gallery, Cove Gallery, Left Bank Gallery, BHA Gallery, The Works Gallery, Off Main Gallery and Frying Pan Gallery. For more information, click here.



Visit the animals! The farm is open daily, dawn to dusk. The friendliest animals have to be Henry, George and Dusty, their goats. Chloe is the Scottish Highland cow, reclining in the pasture. Despite her size, she is quite gentle but with those long horns, you don’t want to get too close. And of course, there are the sheep, donkeys and chickens. Come visit all of them. After you have seen the animals, walk out the boardwalk into Black Flats Marsh with Chapin Beach dunes to the west or left and beyond them, Cape Cod Bay. 375 year-old Taylor-Bray Farm (Est. 1639) is one of the oldest farming sites in the country, and has been run as a successful public-private partnership between the Town of Yarmouth and the Association. Generous funding from the town’s Community Preservation Grant Program has been a key to the farm’s 21st century revival. There are no fees at the farm, but your donations would be greatly appreciated. For more information, click here.



The Fall Festival at Taylor-Bray Farm with hayrides along the Don McIntyre Trail, fresh apple cider, picking pumpkins, and old time games for kids is on October 8, 2022. Pumpkins, gourds, calendars, as well as Taylor-Bray Farm T-shirts, hats, activity books and crafts are on sale. Enjoy hot dogs, apple cider, apple cider donut holes and candy corn Rice Krispie treats. For more information, click here.


Truro Vineyards Winery/Distillery Tour

Owned and operated by the Roberts Family, Truro Vineyards and South Hollow Distillery is perched between the Atlantic Ocean and Cape Cod Bay. They love crafting premium wines and spirits for your enjoyment and creating a peerless destination for visitors. Enjoy tastings, wines by the glass or a cocktail while having lunch from their food truck run by Blackfish Restaurant. New this season they are offering complimentary winery/distillery tours Monday-Friday at 11am. If you would like to do a tasting after the tour, please click here to book your table for 11:30am or later! If reservations are full, they always accept walk-ins that have access to a walk-up bar for cocktails, wines by the glass where can still order from the food truck.


Vinegrass Music Festival in Truro

The 8th Annual Vinegrass Music Festival will be held on Sunday, October 2, 2022. Come listen to Sigard Hollow, Driftwood, Rachel Baiman, and Golden Oak at the intimate & bucolic Truro Vineyards as they continue their tradition in showcasing the sounds of Americana, Bluegrass, & Folk, otherwise known as American Roots Music. Past bands like Mandolin Orange, Lil’ Smokies, and Yarn have graced their stages and gone on to sell out Red Rocks, play Merle Fest and continue to push the boundaries of American Roots music. Beverages available for purchase include Truro Vineyards line of wine, Twenty Boat Rum, and Dry Line Gin. KIDS UNDER 12 YEARS OLD ARE FREE – RAIN OR SHINE – VENDORS – DANCING – ALL ARE WELCOME!!! For more information, click here.



This year’s festival will be held October 8-10, 2022. Founded in 1978 by a local South Yarmouth resident in the hopes of creating community spirit and pride in the Town of Yarmouth. Presented annually on Columbus Day weekend, the festival is the result of a tremendous effort by a small, volunteer committee. The festival has grown into a gala event which boasts a craft fair of more than 125 crafters from all over the country, continual musical entertainment, high‐quality children’s events, nature shows, a kayak and canoe race, pie‐eating contests, beach bonfire, road race, rides and games, and fireworks display. By bringing together our townspeople and tourists alike, they have captured a warm, fun‐loving, and FREE event for all to take part in and enjoy. For more information, click here.



Nothing says fall as going to pick your own apples while enjoying the crisp autumn air on Cape Cod. Founded in 1916, the farm stand offers a variety of homegrown vegetables and fruits, including apples, pears, and sweet corn, in season, from the 40-acres behind the stand. There are also freshly baked pies, preserves, honeys, gourmet mustards, flowers and more. The beautiful walk to the orchard for apple picking is approximately a quarter mile, taking about 5-10 minutes. They recommend bringing a wagon to cart children to the orchards or to carry your apples and pumpkins back to your vehicles. Follow their Facebook page (click here) to see when each variety is ripening so you can better plan your apple-picking trip. For updates on days/times, before heading out we suggest checking their Facebook page, or their website or calling 508-888-0690.



This year, the festival is behind held November 2-6, 2002. The theme of the festival is CELEBRATE PORTUGAL! Provincetown has a great history with Portuguese culture and in line with the 75th anniversary of the blessing of the fleet, they decided this year was perfect to show off Portugal’s flavors! And not only Portugal, but the entire IBERIAN PENINSULA will be the inspiration for specialty events throughout the 2022 festival. This never limits, only enhances. Global wines and diverse menus will shine as they do each year! For more information, click here.



As cranberry harvesting season on Cape Cod occurs from September to December, autumn is the best time for a Cranberry Bog tour. Depending on when you go, expect to see cranberries ready for harvest floating on the surface of the bog, with fall foliage serving as the backdrop. For a list of cranberry bogs on the Cape, click here.



Available until Columbus Day in October, a Lighthouse Harbor Tour with Bay Spirit Tours offers a great vantage point to see some of the Cape’s loveliest lighthouses and other local points of interest, including the Kennedy Compound in Hyannisport. As an added bonus, your harbor tour will provide you with some great glimpses of the leaves turning color on the shore, too. Dress in layers, it can get a little chilly out on the water! For more information on a tour, click here.



Relax and enjoy the spectacular views from the decks of the “Lobster Roll” dinner cruise ship through Columbus Day. Glide through the calm waters of Sesuit Harbor and into the serene beauty of Cape Cod Bay with its incredible sunsets and picturesque coastline. Let us tempt you with your choice of fine foods artfully prepared on board. Our state of the art galley has been designed to prepare the freshest menu items available. Enjoy your favorite frozen drink, cocktail, wine or beer from either of the two upper or lower deck bars. Reservations are strongly recommended however, walk ons are welcome. Planning a Birthday Party ~ Anniversary ~ Wedding ~ Rehearsal Dinner ~ Company Outing Family Reunion ~ Memorial Service ~ Fundraiser? Whether it’s Brunch, Lunch, Sunset Dinner or just a Cocktail Cruise, the S.S. Lobster Roll offers the perfect setting for your special event! For more information on a cruise, click here.



The next time you’re looking for a fun fall getaway on Cape Cod, be sure to check out our boutique collection of vacation homes for your autumn vacation destination by clicking here!



Serene, Tranquil Setting
If you love the “feel” of a traditional Cape Cod vacation, then this exceptional property in East Dennis that sleeps 17 offers just that and more. Providing a mesmerizing setting with acres of natural beauty bordering Sesuit Neck’s salt meadow with magnificent marsh views, The Pearl at Sesuit Neck takes you a step back in time, but with all the amenities of today! This is a true getaway location: with a serene, tranquil setting where you can relax, and get into vacation mode. Featuring an inground pool, several firepits and a grill, 2 kitchens, and 2 living rooms, you don’t ever have to leave this peaceful location if a staycation is what you seek.

Spend Your Days Outdoors
If you wish to get out and explore, all the main attractions of the Cape are a short drive away. Or spend a day sunbathing and walking the shore at one of several of the best beaches in Dennis on the bay side of the Cape. If you wish to stay close and connect with nature, this neighborhood invites bike riding, long walks, and leisurely strolls, and also accesses open space conservation trails that will take you on a pleasant walk bordering Quivet Marsh at its headwaters for bird watching and more.

Intimate Weddings, Family Reunions, Holiday Gatherings, Group Guest Quarters
This location makes an ideal spot for small gatherings, where everyone is guaranteed to have a memorable time. The Pearl offers space for games, talks, dining and time spent with some of nature’s more peaceful surroundings, plenty of open space for kids to run around, and while adults relax, recharge and reconnect. The unique character of this traditional New England heritage location provides a sense of living history, but with modern day conveniences.

Corporate, Workshop or Spiritual Retreats
Check-in for a long weekend of relaxation and rejuvenation with the most beautiful of surroundings, or plan a longer stay. Whether you are looking for a peaceful getaway, a place to retreat and reconnect with nature, or run a workshop, this location will more than meet your needs. To learn more about this property and its availability, click here.


508.420.4200 627 South Main Street, Centerville, MA 02632

LIVE THE CAPE LIFE YOU IMAGINE. We can make it happen.