As temperatures fall and leaves change colors, the new season on Cape Cod changes our vibe. We locals love our visitors, but by summer’s end, we love the thought of fall even more, and if your journey brings you to our doorstep at this time of year, we can promise a different kind of vacation experience. This local’s guide to Chatham is an opportunity to share our love for our Cape home with you and is filled with hints, tips, and all manner of Chatham, MA activities to make your stay shine bright!
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Cooler Temperatures and Smaller Crowds
It never gets really hot on Cape Cod, but that does not mean we don’t appreciate the cooler temperatures of the new season. Nights may get a little frosty, and unlike other places, we can actually wear all those new fall clothes advertised in the stores. (Something to keep in mind when packing.)
The first taste of a pumpkin spice latte purchased from Three Fins Coffee & Cacao Factory is always the sweetest, and falling asleep to a lovely fire in the primary suite of some of our Pretty Picky Properties luxury retreats is sure to be one of your favorite Chatham, Massachusetts activities. Smaller crowds ensure that you will also enjoy beaches that are wide open, shorter wait times in restaurants or pubs, and an extra dose of serenity that accompanies this crisp new season.
Beach Strolls, Harbor Views, and Lighthouse Stops
Grab a jacket from your room and head to the closest beach to watch the sunset. Hardings Beach, located in West Chatham, is one of our favorite places to visit for a sunset beach stroll, offering unobstructed views of the most beautiful sight on earth. If you stroll far enough (just about a mile), you can enjoy the beauty of Stage Harbor Lighthouse, built in 1880. Today, the lighthouse is a private residence and not open to the public, but because lighthouse visits are a popular Chatham activity for kids, Chatham Lighthouse may be where you want to visit next.
There are actually 3 lighthouses in Chatham: Stage Harbor, Monomoy, and the only one you can actually climb to the top of, Chatham Lighthouse. Built in 1808, this gorgeous white tower has recently finished renovations and is now offering tours once again. If you visit during the fall months, you will have to be content with taking pictures from the ground, as tours are only held in June, July, and August.
Chatham Fish Pier Viewing Deck, 99-1 Barcliff Avenue Extended
Every beach town offers that one place where the views of the harbor, boats, and sea life are best, and in Chatham, that place is the Chatham Fish Pier Viewing Deck. This is where the fishing boats bring in their catch each day, selling their bounty to the Chatham Pier Fish Market. The pier itself, however, serves as a wonderful viewing spot, especially if you want to catch sight of seals. There are seal watching tours you can take if you want some info on the playful creatures, but the viewing deck offers a casual, laidback adventure that won’t cost anything.
Seasonal Wildlife and Nature Highlights
Exploring the natural beauty of Cape Cod may be your favorite Chatham, Massachusetts activity. Obviously, fall is leaf peeping season, and the fiery leaves will take your breath away as you take photo after photo. We urge you to put your camera down, at least for a minute, as you explore the colorful trails of the Monomoy National Wildlife Refuge. Feel the quiet of your surroundings, savor the serenity of the wooded areas, and live in the moment. You can pick up your camera again, perhaps snapping the perfect picture of the birds as they begin their migration to warmer waters. Autumn is the peak time for the Atlantic Flyway, and you may be able to witness sand pipers, falcons, and sea ducks beginning their journey.
Shop, Dine, and Explore Main Street
The best secret about visiting Cape Cod when it isn’t summer is the knowledge that not only are shops emptier and wait times at restaurants shorter, but costs are lower. You can’t take a vacation without shopping, dining, and exploring Main Street, all popular off-season Chatham, MA activities.
Beacon & Buoy
Beacon & Buoy is one of our town’s newest restaurants, open for breakfast, lunch, and dinner. We often crave their Coconut Curry Mussels or their Wild Mushroom Farro Risotto. Our favorite breakfast item is their short rib breakfast, and none of us can leave without at least sharing their Chocolate Crème.
- Address: 1200 Main St, Chatham, MA 02633
- Hours: 8 AM to 3 PM Tuesday-Saturday
- 5 PM to 9 PM Tuesday-Thursday
- 5 PM to 10 PM Friday-Saturday
- Dinner Menu
Yankee Ingenuity
When you first arrive in town, it might be our historic and charming Main Street that will capture a piece of your heart. The best restaurants and shops can be found on Main Street, including one of our most beloved shops, Yankee Ingenuity. They piqued our interest with the name and captured our hearts with their unique merchandise. We bet you didn’t know you needed a cold cast bronze and resin lounging mermaid, but once you see theirs, you won’t be able to get it out of your mind!
- Address: 525 Main St, Chatham, MA 02633
- Hours: 9 AM to 9 PM (Opens 10 AM Sunday)
Easy Day Trips and Attractions
A day trip to Nantucket Island may be another of those Chatham, Massachusetts activities that you never knew you needed to experience. Booking a high-speed passenger ferry not only cuts down travel time (traditional ferries take 2.5 hours) but can also be an exciting part of the adventure. You will have to head to Hyannis for a Hy-Line Cruise ferry ride, and reservations are required year-round.
Other day trip options include Provincetown, located just 36 miles outside of Chatham. The Pilgrim’s Monument and Pilgrim’s First Landing Park are two activities you may enjoy during your day trip to Provincetown. You can also head to Brewster, known for its tidal flats, the 19th-century Stony Brook Grist Mill, and a large selection of antique stores.
Book Your Chatham Vacation Rental and Enjoy Cape Cod After the Summer
A visit to Chatham after summer’s end will be an experience you will never forget, and our Chatham seasonal sanctuaries will be the perfect home base for each adventure. All of the Chatham, MA activities we have listed here will tire you out, and coming home to Pretty Picky Properties will help perk you right back up. Reserve your favorite retreat today!
