We may primarily be known as a summer vacation destination here on Cape Cod, but we at Pretty Picky Properties would like to tell you a little bit about how fall can be your favorite season to visit. The crowds will have returned to their real lives, the wait times at restaurants will be shorter, and the vibrant colors of autumn will add a postcard quality feel to the landscape. We’ve created this ultimate guide to fall in Cape Cod that will give you all the ideas on what to do for each of the seven days of your vacation in paradise, and when you get to come home to our seasonal sanctuaries at the end of every adventure, you truly will understand why this is a wonderful season to visit.
Day 1: Harwich Adventures
First, let’s talk weather. Fall temps can range from 70+ degrees in the early days to 35+ degrees as winter grows closer, but for the purpose of day one, we are going to assume that your visit is in September, when the weather is practically perfect. The leaves won’t be changing as of yet, but the beautiful sunny days and warm temperatures will allow you to extend summer fun just a little longer, and beach days will be a major part of your adventures. Red River Beach may be the one where you choose to play, but Harwich is home to a large number of beaches, all of which will bring you joy.
Meals to Remember in Harwich
The food you eat on vacation often plays a large part in the memories you enjoy, and although our Pretty Picky Properties fall retreats do offer fully equipped kitchens, we encourage you to explore the culinary landscape of Cape Cod. Breakfasts and lunches at Ruggie’s, located at 707 Main Street, has been a local tradition for about 14 years now, offering hearty meals that are locally sourced and made with the freshest of ingredients. For dinner, the Mad Minnow, found at 554 MA-28, is a local gastropub serving pub grub and the best lobster mac and cheese you have ever tasted.
Harwich Cranberry Arts & Music Festival, Mid-September, 100 Oak Street
As if this first day in Harwich hasn’t been chock-full of adventures, if your journey brings you here the week before the official start of fall, the Harwich Cranberry Arts & Music Festival, offers juried crafters, kid’s activities, live music, dance floors, and food and beverage trucks, all crafted to create an event that will make you happy to be alive.
Day 2: All That Yarmouth Has to Offer
Yarmouth is one of the oldest towns, known for its Cape Cod fall activities, beautiful beaches, and for the breweries that have become a major part of the landscape. Starting your day out with a sunrise walk along the shores of Sea Gull Beach will help center you and prepare you for a day of fun and magic, and when the sky has regained its azure color of daylight, why not head over for breakfast at Piccadilly Café & Deli for a delicious breakfast? Located at 1105 MA-28, this amazing breakfast and lunch spot is famous for its benedicts, serving 12 different kinds, including our personal favorite, their crab cake benny. After breakfast, families with kids may want to explore the Whydah Pirate Museum, located at 674 MA-28, which offers a peek into the world of the rascally buccaneers that once ruled the waters, including a fascinating Pirate Ship Exhibition that will delight your tiniest travelers.
When the Dinner Bell Rings
The seafood you eat here will be the freshest and sweetest you have ever enjoyed, and even as we do offer a selection of haute cuisine restaurants that will be perfect for your special occasion meals, most restaurants will be casual, welcoming, and will offer meals that are hearty, simple, and filled with taste and the Skipper Restaurant and Chowder House, 152 S Shore Drive, promises to be the ideal example. Offering a classic taste of Cape Cod, this is a seasonal restaurant, but most of our seasonal restaurants stay open through mid-October, so be sure to stop by and explore their seafood-centric menu.
Yarmouth Seaside Festival
Celebrating cooler days, art, music, and delicious foods, there will be kids’ activities, a 5K, a canoe and kayak race, and a sand sculpture contest in which every guest is invited to participate. Join the fun Columbus Day weekend at Joshua Sears Memorial Field.
Day 3: Savoring Sandwich
No, we aren’t talking about America’s favorite handheld. We are, of course, discussing the wonders of Sandwich, and the third day of your fall adventures promises to be your favorite. This town is officially the oldest town on Cape Cod, and its history plays a large part in its popularity for tourists. Today’s adventures, however, are going to lean towards more natural ones and because there will be a lot of walking, we suggest starting out with the heartiest of breakfasts, with Café Chew being our recommendation for today. Located at 4 Merchants Road, a so-so meal has never graced the tables of this local favorite. EVERYTHING will be your favorite, especially when accompanied by their herb & onion home fries. Famous for their breakfast sandwiches, we encourage you to sample their Portuguese Sailor, made with eggs, cheddar, and linguica sausage stuffed into a Portuguese roll.
Now for the Fun Part
If your Fall in Cape Cod journey brings you to Sandwich after mid-October, we suggest that peeping leaves will be your most memorable activity. The best way to see the changing of the leaves is by taking a hike along the walking trails that go along Scorton Creek. The Scorton Creek and Hoxie Pond Loop is an easy stroll lasting just under a mile, and the trees that offer a summer canopy over the path will be dressed in their most vibrant fall colors. Keep your camera handy during this hike because there will be a plethora of photo opportunities that will turn into pictures that are worthy of framing. When dinner time rolls around, although we usually recommend a seafood restaurant, today we think a large pizza from the Brown Jug will hit the spot! Located at 155 Main Street, their pizzas offer a unique blend of ingredients sure to sate the appetite of the hungriest traveler.
Annual Pumpkin Fest
Held on the lawn of the Sandwich Glass Museum, the pumpkin festival allows travelers to purchase pumpkins that will never rot, serving as a souvenir that will remind them of the good times they had on Cape Cod in the fall. The glass pumpkins range in size and color and the hardest part of picking your favorite will be narrowing down the choices. You can experience these amazing works of art in Mid-October.
Day 4: Chatham Awaits
Known for its Chatham Lighthouse, if you happen to be here in the month of September, we are definitely going to recommend taking a tour; they are open for tours every other Wednesday through the end of the month. If you aren’t visiting during tour hours, you will still enjoy wandering around the outside, taking family photos that will be perfect for your annual Christmas card, and if you really want those pictures to shine, we encourage a sunset visit to the lighthouse.
Breakfast of Champions
If cooking breakfast in your fully equipped Pretty Picky Properties kitchen doesn’t sound like something you want to do, but you wake up on day four feeling extra hungry, the Chatham Filling Station is up to the challenge of conquering your hunger. Located at 75 Old Harbor Road, their pulled pork benedict will fill your tank and give you the energy you need for your Chatham adventures. The blueberry pancakes are the best in town too! After breakfast, if you aren’t heading to the Chatham Lighthouse, a visit to the AWSC Shark Center, 235 Orleans Road, is sure to give your family something fascinating to talk about for years to come.
Special Occasion Dinner at the Impudent Oyster
Remember the special occasions we were talking about earlier? The Impudent Oyster is where we suggest you go to celebrate, offering an elevated seafood menu that includes a large variety of raw oysters, and featuring a bar that is always hopping. Visit the venue at 15 Chatham Bars Avenue.
Pop Film Festival
In a world that is slowly learning that recycling and renovating saves the earth, Chatham’s POP Film Festival (Protect our Past) offers a series of films and documentaries that celebrate the preservation, restoration, and conservation of the historic properties that dot the landscape. Watch some classics in early October at the Chatham Orpheum Theater.
Day 5: Obviously Orleans
Military buffs geek out over knowing that Orleans is the only US site attacked by Germans during World War II, as well as suffering an attack on Rock Harbor during the war of 1812, making a visit to the Coast Guard Motor Lifeboat CG-36500 located in Rock Harbor an excellent idea. This floating museum was built in 1946, and although it was nearly lost in the passage of time, was restored after being acquired by the Orleans Historical Society in 1981. Another military site you may want to visit on your 5th day in paradise is the French Cable Station Museum, located at 41 S Orleans Road and open on weekends (including Fridays) through the end of September. Offering a peek into the history of telegraphs and their importance during war times.
Homeport Restaurant
Sometimes you find the perfect restaurant, one that serves the best breakfasts, lunches, and dinners, and when in Orleans, that restaurant would be Homeport Restaurant. Serving all three meals every day of the week except Tuesdays when they close at 2, Homeport has been a local favorite for over 50 years. As you can imagine, their menu is expansive and filled with all-American favorites, and because we have never experienced a bad meal here, we encourage you to try it all! They are located at 55 Main Street and open daily at 6 AM.
Outermost Roots & Blues Festival
Two days of music, beach, fun, food and drink; do we really need to say anything more about this fun annual festival? Probably not, but we will say that VIP tickets provide access to private bathrooms, better viewing areas, and a collectible poster! Check out the fun at Nauset Beach in Mid-October.
Day 6: Beaming in Brewster
As the end of your Cape Cod journey draws ever nearer to a close, there are still some fall adventures to experience, and your Brewster adventures are going to bring you joy. Known for its seafaring captains, your autumn activities may include a day on the links at Captain’s Golf Course, located at 1000 Freeman’s Way. Offering two 18-hole courses, Port and Starboard, each hole on each course is named after a different Cape Cod sea captain. Their 19th Hole, also known as the Freeman’s Grill, is open every day, providing delicious food and the opportunity to buy drinks for the house when you achieve the magical hole-in-one.
Chillingsworth Restaurant
Famed for its French food and for welcoming acclaimed super chef Julia Childs at its table, Chillingsworth Restaurant is another special occasion restaurant that we highly recommend. Housed in the 300-year-old Chillingsworth Foster Estate at 2449 Main Street, it has been a shining star on our culinary landscape for over 40 years.
