Roberta's Guidebook
Food scene
Wonderful and charming restaurant at the regional airport. Open 7-2pm and they open for dinner some nights in the summer. Often a wait but worth it! One of our favorite places.
46 locals recommend
Hangar B Eatery
240 George Ryder RdWonderful and charming restaurant at the regional airport. Open 7-2pm and they open for dinner some nights in the summer. Often a wait but worth it! One of our favorite places.
A great place to go and enjoy the beautiful grounds. Good for a drink or lunch down by the pool / ocean.
97 locals recommend
Chatham Bars Inn
297 Shore RdA great place to go and enjoy the beautiful grounds. Good for a drink or lunch down by the pool / ocean.
The market where we buy our fish. Also a restaurant great for local favorites like fish and chips, clam chowder but also sushi and rice bowls. Yum!
46 locals recommend
Mac's Chatham Fish & Lobster
Massachusetts 28The market where we buy our fish. Also a restaurant great for local favorites like fish and chips, clam chowder but also sushi and rice bowls. Yum!
Cute farm stand store with produce, flowers, baked goods, cookies, etc. Always something fun to pick up here.
8 locals recommend
Chatham Bars Inn Farm
3034 Main StCute farm stand store with produce, flowers, baked goods, cookies, etc. Always something fun to pick up here.
A watering hole in Chatham known for its clam chowder. An institution.
140 locals recommend
Chatham Squire
487 Main StA watering hole in Chatham known for its clam chowder. An institution.
Same owners as Mac’s on Route 28, but the original and much more beachy location up the Cape.
99 locals recommend
Mac's Shack
91 Commercial StSame owners as Mac’s on Route 28, but the original and much more beachy location up the Cape.
A new and popular sandwich spot. Across from Chatham Bars Farmstead.
8 locals recommend
The Kitchen Cafe Brewster
2671 Main StreetA new and popular sandwich spot. Across from Chatham Bars Farmstead.
You can’t get a closer restaurant to the house than Pisces - just at the end of the street! They changed ownership this year but it’s been a favorite of ours for years!
27 locals recommend
Pisces
2653 Main StYou can’t get a closer restaurant to the house than Pisces - just at the end of the street! They changed ownership this year but it’s been a favorite of ours for years!
Love getting take out from this yummy Italian market. Coffee, pastries, paninis, lasagne and way more!
Cibo Italian Kitchen & Market
15 Cove RoadLove getting take out from this yummy Italian market. Coffee, pastries, paninis, lasagne and way more!
Popular restaurant close by on route 28. They have a large menu and great drinks.
25 locals recommend
Pate's Restaurant
1260 Main StPopular restaurant close by on route 28. They have a large menu and great drinks.
Sightseeing
Beautiful beach and a historic lighthouse. You can walk for quite a ways but the water is chilly!!
73 locals recommend
Lighthouse Beach
30 Main StreetBeautiful beach and a historic lighthouse. You can walk for quite a ways but the water is chilly!!
You fall out of our house onto this beach. The water is warm and protected, being Nantucket Sound. Walk to the Point collecting shells along the way. Take the path back for a change in scenery and admire the marsh from a different angle.
10 locals recommend
Forest Beach
You fall out of our house onto this beach. The water is warm and protected, being Nantucket Sound. Walk to the Point collecting shells along the way. Take the path back for a change in scenery and admire the marsh from a different angle.
Take a trip up the Cape and stop here for a beautiful view and a bit of interesting Cape history (the Titanic sent it’s distress signal to this radio tower!). The dunes have eroded over the years but seeing the National Seashore from above is a special view.
22 locals recommend
Marconi Wireless Station
Take a trip up the Cape and stop here for a beautiful view and a bit of interesting Cape history (the Titanic sent it’s distress signal to this radio tower!). The dunes have eroded over the years but seeing the National Seashore from above is a special view.
Watch the fishing boats come in and unload their catch. The seagulls and seals live for it!
77 locals recommend
Chatham Pier Fish Market
45 Barcliff AveWatch the fishing boats come in and unload their catch. The seagulls and seals live for it!
Shopping
Chatham Candy Manor
484 Main StYou can’t leave Chatham without a trip to the Candy Manor!!
At Home Again
1705 Main StreetWell curated second hand shop full of furniture and decor.
Puritan Cape Cod
573 Main StGreat selection of cute clothes - very Cape-y :-)
Love this little gem in Orleans. Great place for a facial if that’s on your vacay to do list.
Supple Apothecary
82 MA-6ALove this little gem in Orleans. Great place for a facial if that’s on your vacay to do list.
Activities
Weekly concerts in the summer. Friday nights. Great for kids. Take a blanket, picnic and a bottle of wine!
11 locals recommend
Kate Gould Park
15 Chatham Bars AvenueWeekly concerts in the summer. Friday nights. Great for kids. Take a blanket, picnic and a bottle of wine!
Chatham As baseball is legendary - a feeder for the major leagues. Check out a game!
Chatham Anglers Baseball
15 Veterans Field RoadChatham As baseball is legendary - a feeder for the major leagues. Check out a game!
Take the ferry over to Nantucket or Martha’s Vineyard for the day!
83 locals recommend
Hy-Line Cruises
220 Ocean StTake the ferry over to Nantucket or Martha’s Vineyard for the day!
This harbor has deep sea fishing, ferries to Nantucket and seal tours daily! 2 miles from the house.
Saquatucket Harbor
This harbor has deep sea fishing, ferries to Nantucket and seal tours daily! 2 miles from the house.
Neighborhoods
Very cute twin for walking around, shopping, eating ice cream and taking in the scene!
129 locals recommend
Chatham
Very cute twin for walking around, shopping, eating ice cream and taking in the scene!
Plan on a whole day to go to Provincetown. Such a cute and quaint town with lots of color and goings on. Eat a flipper at the Portuguese Bakery, whale watch is you’re feeling lucky…there’s a ton to do.
328 locals recommend
Provincetown
Plan on a whole day to go to Provincetown. Such a cute and quaint town with lots of color and goings on. Eat a flipper at the Portuguese Bakery, whale watch is you’re feeling lucky…there’s a ton to do.
Beautiful, historical town. Heritage plantation is there with gorgeous flowers.
31 locals recommend
Sandwich
Beautiful, historical town. Heritage plantation is there with gorgeous flowers.