Cheryl’s guidebook
City/town information
Bay beaches, bike trail, unique restaurants, best coffee shop on the lower Cape, numerous ponds for swimming, kayaking, and even a pickle ball court!
13 locals recommend
Brewster
Bay beaches, bike trail, unique restaurants, best coffee shop on the lower Cape, numerous ponds for swimming, kayaking, and even a pickle ball court!
Lots open all year round - Skaket (bay) and Nauset (ocean) are quintessential Cape Beaches. Off season watch the kite boarders daring feats
19 locals recommend
Orleans
Lots open all year round - Skaket (bay) and Nauset (ocean) are quintessential Cape Beaches. Off season watch the kite boarders daring feats
With ocean views hiking trails and the bike trail running through it, it’s hard to avoid Harwich - and why would you want to?
13 locals recommend
Harwich
With ocean views hiking trails and the bike trail running through it, it’s hard to avoid Harwich - and why would you want to?
Chatham is the quintessential Cape Cod Village right in the elbow of the Cape with harbor and ocean views, light house shops restaurants - it has it all
129 locals recommend
Chatham
Chatham is the quintessential Cape Cod Village right in the elbow of the Cape with harbor and ocean views, light house shops restaurants - it has it all
Sip a cup of coffee with the local guys and get all the local inside story
46 locals recommend
The Brewster Store
1935 Main StSip a cup of coffee with the local guys and get all the local inside story
Don’t miss a trip to Wellfleet for the galleries, little shops, great restaurants, scenic harbor, marshes - it’s got it all. The general store has a great selection of just about everything you need
To have a wonderful Cape vacation from food to books to wine.
54 locals recommend
Wellfleet
Don’t miss a trip to Wellfleet for the galleries, little shops, great restaurants, scenic harbor, marshes - it’s got it all. The general store has a great selection of just about everything you need
To have a wonderful Cape vacation from food to books to wine.
This beautiful tip of Cape Cod not only has unequalled natural beauty, but it is known as one of the friendliest LGBTQA towns in the world with great shops galleries restaurants beaches waterfront theaters serviced by the ferry from Boston - it is a destination!! Don’t miss it. Off season some things are closed
328 locals recommend
Provincetown
This beautiful tip of Cape Cod not only has unequalled natural beauty, but it is known as one of the friendliest LGBTQA towns in the world with great shops galleries restaurants beaches waterfront theaters serviced by the ferry from Boston - it is a destination!! Don’t miss it. Off season some things are closed
This is a great place for local information, checking out a great book or puzzle, sitting in a sun-filled room or on an outdoor patio or buying a used book or puzzle.
14 locals recommend
Brewster Ladies' Library
1822 Main StThis is a great place for local information, checking out a great book or puzzle, sitting in a sun-filled room or on an outdoor patio or buying a used book or puzzle.
Eastham Public Library
190 Samoset RdKnown as one of the most beautiful libraries on the Cape
Beautiful architecture, interesting people, great study areas
30 locals recommend
Provincetown Library
356 Commercial StBeautiful architecture, interesting people, great study areas
Chatham Pier Fish Market
45 Barcliff AveIconic Chatham sight
Food scene
Best cup of coffee on the Lower Cape and a real hangout any season of the year
69 locals recommend
Snowy Owl Coffee Roasters
2624 Main StBest cup of coffee on the Lower Cape and a real hangout any season of the year
Very reliable seafood most months of the year - May be closed in Jan to mid feb. good local seagood
63 locals recommend
The Brewster Fish House
2208 Main StVery reliable seafood most months of the year - May be closed in Jan to mid feb. good local seagood
The season begins in May and ends a couple weeks after Labor Day but great seafood shack which also has pretty good ice cream
30 locals recommend
Kate's Seafood
284 Paine's Creek RdThe season begins in May and ends a couple weeks after Labor Day but great seafood shack which also has pretty good ice cream
This is a popular destination so I’ve included it here. It has a nice view of the marshes. The cuisine is average. One is aware that the service is mostly about pushing up your tab. Getting a reservation is tough- off season is easier.
62 locals recommend
The Marshside
28 Bridge StThis is a popular destination so I’ve included it here. It has a nice view of the marshes. The cuisine is average. One is aware that the service is mostly about pushing up your tab. Getting a reservation is tough- off season is easier.
Lively Italian cuisine courente nice fireplace and bar. Cozy winter spot
87 locals recommend
Scargo Cafe
799 Main StLively Italian cuisine courente nice fireplace and bar. Cozy winter spot
I’m not a pizza person but I see a LOT of their boxes in the recycling bin.
26 locals recommend
Stone L'oven Pizza
280 Underpass RdI’m not a pizza person but I see a LOT of their boxes in the recycling bin.
Best close blue collar pizza. Also delivers but even though they say they do slice - they don’t - just call
32 locals recommend
The Brewster Book Store
2648 Main StBest close blue collar pizza. Also delivers but even though they say they do slice - they don’t - just call
People love the baked goods and there’s also a second hand shop. Check ahead for hours - usually just open on weekends.
9 locals recommend
Hopkins House Bakery and Gift Shop
2727 Main StPeople love the baked goods and there’s also a second hand shop. Check ahead for hours - usually just open on weekends.
Great seafood shack and food soft serve. Plenty of outdoor seating. Cuisine goes above fried to grilled meals as well
37 locals recommend
Captain Frosty's
219 Main StGreat seafood shack and food soft serve. Plenty of outdoor seating. Cuisine goes above fried to grilled meals as well
The Salmon Burger is a great deal for around $9-10 - comes w fries and slaw / but there are other great offerings as well. Sits on the Swam river with a lovely view. Call ahead to make sure they are open
58 locals recommend
Kream 'n Kone
961 Main StThe Salmon Burger is a great deal for around $9-10 - comes w fries and slaw / but there are other great offerings as well. Sits on the Swam river with a lovely view. Call ahead to make sure they are open
Sir Cricket's Fish & Chips
38 MA-6AGreat hole-in-the-wall seafood place open year round.
Wild Goose Tavern
512 Main StGreat trendy spot right in the heart of town
The Hot Chocolate Sparrow used to be a wonderful year round hangout but post Covid there is no longer indoor seating - it’s still a spot for coffee sweets and light meal items right on the rail trail in the center
of Orleans great place to park and explore the town. It affectionately known in our family as The Dirty Bird
58 locals recommend
Hot Chocolate Sparrow
5 Old Colony WayThe Hot Chocolate Sparrow used to be a wonderful year round hangout but post Covid there is no longer indoor seating - it’s still a spot for coffee sweets and light meal items right on the rail trail in the center
of Orleans great place to park and explore the town. It affectionately known in our family as The Dirty Bird
Nice variety of breakfast goods and bars, cookies, pastries and cakes. Light lunch items as well.
20 locals recommend
Cottage Street Bakery
5 Cottage StNice variety of breakfast goods and bars, cookies, pastries and cakes. Light lunch items as well.
Great spot for donuts or a big breakfast through lunch.
47 locals recommend
Hole In One Breakfast & Lunch
98 MA-6AGreat spot for donuts or a big breakfast through lunch.
This is another one of those restaurants - go for the view. Busy in season
90 locals recommend
Brax Landing Restaurant
705 MA-28This is another one of those restaurants - go for the view. Busy in season
Buca's Tuscan Roadhouse
4 Depot RdThis restaurant gets universal rave reviews in Harwich
Mac's Chatham Fish & Lobster
Massachusetts 28Macs does seafood right.
Until his third year of med school, we celebrated my sons birthday here every year - his fav place and a Wellfleet institution. Eat overlooking the lovely harbor and gaze out toward Ptown
35 locals recommend
Mac's On the Pier
265 Commercial StUntil his third year of med school, we celebrated my sons birthday here every year - his fav place and a Wellfleet institution. Eat overlooking the lovely harbor and gaze out toward Ptown
Seafood shack with more Unfried menu items. Longer season than most. Covered dining section
22 locals recommend
JT's Seafood Restaurant
2689 Main StSeafood shack with more Unfried menu items. Longer season than most. Covered dining section
Kream N' Kone Restaurant
1653 Main StSeafood shack with large covered dining area
Chatham Filling Station
75 Old Harbor RdNice breakfast and lunch place known for their popovers
This restaurant is a favorite of friends and guests alike. Beautiful setting. Eating outside in the evening after the crowds have gone - lovely!
60 locals recommend
Bookstore & Restaurant
50 Kendrick AveThis restaurant is a favorite of friends and guests alike. Beautiful setting. Eating outside in the evening after the crowds have gone - lovely!
Guests like the big breakfasts here. Easy drive just over the Dennis line on 6a
48 locals recommend
Grumpy's
1408 Main StGuests like the big breakfasts here. Easy drive just over the Dennis line on 6a
Pizza and sandwiches all year round!! Great view of pleasant lake. Take out only
10 locals recommend
Pleasant Lake Pizza Shark
403 Pleasant Lake AvePizza and sandwiches all year round!! Great view of pleasant lake. Take out only
Great place for breakfast lunch pastries or just learning where the locals hang
16 locals recommend
Chatham Perk
307 Orleans RdGreat place for breakfast lunch pastries or just learning where the locals hang
Rock Harbor Grill
18 Old Colony WayGood family place and Local favorite with variety of cuisines
Impudent Oyster
15 Chatham Bars AveClassy Chatham eatery
Fine with a stunning view of Pleasant Bay. Highly recommend cocktails on the terrace
59 locals recommend
Wequassett Resort and Golf Club
2173 MA-28Fine with a stunning view of Pleasant Bay. Highly recommend cocktails on the terrace
Chatham Bars Inn
297 Shore RdElegant dinner spot with a view
Larry's PX
1591 Main StThe diner locals prefer
This is supposed to be the best chef on the Cape who buys only the best ingredients daily. Can’t wait to have an occasion to go. Italian in the finest sense.
20 locals recommend
Gerardi's Cafe
902 MA-28This is supposed to be the best chef on the Cape who buys only the best ingredients daily. Can’t wait to have an occasion to go. Italian in the finest sense.
Eat Cake 4 Breakfast
26 Wampum DrChillingsworth Restaurant
2449 Main StRenowned as one of the finest restaurants on the Cape
Local hangout swelled by tourists in-season. Curious mix food- meh. Authentic Chatham experience- 👍👍
140 locals recommend
Chatham Squire
487 Main StLocal hangout swelled by tourists in-season. Curious mix food- meh. Authentic Chatham experience- 👍👍
While not my fav seafood shack - it does have pretty good food. My reservation - sometimes long lines, crowded dining experience. It is right on Sesuit Harbor next to the marina. Last time I went - pretty decent lobster roll
167 locals recommend
Sesuit Harbor Cafe
357 Sesuit Neck RdWhile not my fav seafood shack - it does have pretty good food. My reservation - sometimes long lines, crowded dining experience. It is right on Sesuit Harbor next to the marina. Last time I went - pretty decent lobster roll
Caroline's Bar and Grill
4380 U.S. 6330-5 Happy hour - buck-a-shuck oysters. Nuf said
Mostly for meat lovers - not cheap - but my Brazilian friends love it!
58 locals recommend
Brazilian Grill
680 Main StMostly for meat lovers - not cheap - but my Brazilian friends love it!
The most lobster in a lobster 🦞 roll for the least price. Take home or sit overlooking Rick harbor
6 locals recommend
Young's Fish Market
113 Rock Harbor RdThe most lobster in a lobster 🦞 roll for the least price. Take home or sit overlooking Rick harbor
Artisan bread and pastries - tough to find on the Cape- a bit expensive but very good quality. The fig bread is a personal favorite
107 locals recommend
PB Boulangerie Bistro
15 Lecount Hollow RdArtisan bread and pastries - tough to find on the Cape- a bit expensive but very good quality. The fig bread is a personal favorite
Parks and recreation
This is one of Massachusetts’ great park gems and offers so many activities walks trails swimming kayaking fishing. I recommend the Flax pond trail which is easily walkable and has frequent pond access. The park goes all the way to the Crosby beach on the other side of art 6a and the wonderful trail above the beach
115 locals recommend
Nickerson State Park
3488 Main StreetThis is one of Massachusetts’ great park gems and offers so many activities walks trails swimming kayaking fishing. I recommend the Flax pond trail which is easily walkable and has frequent pond access. The park goes all the way to the Crosby beach on the other side of art 6a and the wonderful trail above the beach
Great bay beach snack bar facilities. I took this picture of kite fliers at the beach off season
56 locals recommend
Skaket Beach
Great bay beach snack bar facilities. I took this picture of kite fliers at the beach off season
Nauset Beach
250 Beach RdThis is the quintessential Cape beach!
On Rt 28 between Orleans and Chatham is an amazing beach harbor fishing spot play place for people of all ages. It’s quite unique but parking is just along the road so get there early in season
8 locals recommend
Jackknife Cove
2019 MA-28On Rt 28 between Orleans and Chatham is an amazing beach harbor fishing spot play place for people of all ages. It’s quite unique but parking is just along the road so get there early in season
Grab a bike and a map at most Cape tourist info spots - and I always have one in the apartment - and see the Cape as you can no other way - up close and personal. Runs from Dennis and Chatham to Wellfleet Truro
36 locals recommend
Cape Cod Rail Trail
Cape Cod Rail TrailGrab a bike and a map at most Cape tourist info spots - and I always have one in the apartment - and see the Cape as you can no other way - up close and personal. Runs from Dennis and Chatham to Wellfleet Truro
Beautiful and unique any time of day or evening. Sometimes a band plays the sun to set - very Key West. You can also catch fishing and party boats here
18 locals recommend
Rock Harbor
Beautiful and unique any time of day or evening. Sometimes a band plays the sun to set - very Key West. You can also catch fishing and party boats here
Long pond has a couple beach/access points. Bring your kayak canoe or whatever boat you have. It’s a lovely place to spend a day
Long Pond Brewster Beach
Long pond has a couple beach/access points. Bring your kayak canoe or whatever boat you have. It’s a lovely place to spend a day
Small local beach. Lots of swimmers in season. Kayaking paddleboarding fishing. Great small pond for all your non motor water activities
Sheep Pond Beach
Sheep Pond DriveSmall local beach. Lots of swimmers in season. Kayaking paddleboarding fishing. Great small pond for all your non motor water activities
This is a wonderful high spot for an expansive view of the inlets of Orleans. You can often see seals basking in the sun below
58 locals recommend
Fort hill trail
This is a wonderful high spot for an expansive view of the inlets of Orleans. You can often see seals basking in the sun below
This is a fun beach for walking at low tide but during the season parking is tight. Off season it’s a wonderful spot to park and view the expanse of beach even on a stormy or snowy day
32 locals recommend
Paines Creek Landing and Beach
143 Cedar Hill RdThis is a fun beach for walking at low tide but during the season parking is tight. Off season it’s a wonderful spot to park and view the expanse of beach even on a stormy or snowy day
Lighthouse Beach
30 Main StreetGreat place for people watching
Big Dogs BBQ
191 MA-6ACandle pin bowling and super bbq - open all year. Great for a winter
Or rainy day!
Shopping
Wonderful comprehensive cook shop open all year round. Great to have such a place in Brewster
Cook Shop
1091 Main StOne of the best cook shops anywhere and loads of fun to explore
This is probably the best boat and nautical equipment store on the lower Cape. Fun to poke around on a rainy day or rent a kayak and take a group tour
18 locals recommend
Goose Hummock Shop
15 MA-6AThis is probably the best boat and nautical equipment store on the lower Cape. Fun to poke around on a rainy day or rent a kayak and take a group tour
This wonderful gallery on the second floor of The Cornfield has a great collection of local artists with many great local scenes. The gallery owner Domonic Boreffi is very knowledgeable and accommodating.
Gallery Antonia
1291 Main StThis wonderful gallery on the second floor of The Cornfield has a great collection of local artists with many great local scenes. The gallery owner Domonic Boreffi is very knowledgeable and accommodating.
Stop and shop, liquor store, TJ Max, CVS, Dollar tree, restaurant. Nearby is Dunkin, cinema, several gas stations, post office. Good place to meet lots of needs
Patriot Square Shopping Center
516 MA-134Stop and shop, liquor store, TJ Max, CVS, Dollar tree, restaurant. Nearby is Dunkin, cinema, several gas stations, post office. Good place to meet lots of needs
Right on the bike trail and in the center of Orleans - they are friendly and comprehensive. Park in the main lot by the Chocolate Sparrow if you plan to stay and see more of what Orleans has to offer
9 locals recommend
Orleans Cycle
26 Main StRight on the bike trail and in the center of Orleans - they are friendly and comprehensive. Park in the main lot by the Chocolate Sparrow if you plan to stay and see more of what Orleans has to offer
Bird Watcher's General Store
36 MA-6ABird watchers swear by this fun spot!
I’m very fortunate to have such a comprehensive liquor store so close by. They won’t be the cheapest but they will usually have what you want. They used to have a lot of tasting carafes set up but It just can’t be done right now
Luke's Super Liquor Stores
15 Lower RdI’m very fortunate to have such a comprehensive liquor store so close by. They won’t be the cheapest but they will usually have what you want. They used to have a lot of tasting carafes set up but It just can’t be done right now
Quirky combination new and used books and the most helpful staff
8 locals recommend
Yellow Umbrella Books
501 Main StQuirky combination new and used books and the most helpful staff
Chatham Candy Manor
484 Main StFun
A wonderful mix that isn’t the usual tourist tschotches - a lot of fun to browse. Something for everyone.
17 locals recommend
Yankee Ingenuity
525 Main StA wonderful mix that isn’t the usual tourist tschotches - a lot of fun to browse. Something for everyone.
This is a must-see in Chatham culture and you can pick up some great seafood too. Subject of many artists
77 locals recommend
Chatham Pier Fish Market
45 Barcliff AveThis is a must-see in Chatham culture and you can pick up some great seafood too. Subject of many artists
Mayflower Shop
475 Main StThis shop has above average merchandise - I always find something unique.
Seafood shopping with a view! Don’t miss. Small restaurant adjacent
6 locals recommend
Young's Fish Market
113 Rock Harbor RdSeafood shopping with a view! Don’t miss. Small restaurant adjacent
Orleans Seafood Market
18 Old Colony WayMy oldest neighbors claim this to be the best! Thursday is discount day
Outdoor shopping area over many streets and blocks featuring chain stores and restaurants as well as some interesting local spots. Download a map of the area before you go because you might think you’ve seen everything when you’ve only seen one part
253 locals recommend
Mashpee Commons
22 Steeple StOutdoor shopping area over many streets and blocks featuring chain stores and restaurants as well as some interesting local spots. Download a map of the area before you go because you might think you’ve seen everything when you’ve only seen one part
Great small market with super variety, good wine selection - take your Vivino app for bargain hunting - great plants and garden shop
26 locals recommend
Friends' Marketplace
57 Main StGreat small market with super variety, good wine selection - take your Vivino app for bargain hunting - great plants and garden shop
One of the neatest general stores on the Cape and located on a great walking shopping street in downtown Wellfleet! You can fine just about everything you need here and have so much fun in the process!
45 locals recommend
Wellfleet Market Place
295 W Main StOne of the neatest general stores on the Cape and located on a great walking shopping street in downtown Wellfleet! You can fine just about everything you need here and have so much fun in the process!
Great market - some say they have the best baked goods of any market of this type on the Cape.
18 locals recommend
Nauset Farms
199 Main StGreat market - some say they have the best baked goods of any market of this type on the Cape.
My favorite small market ( CVS is next door). Super fresh seafood and sushi. The smoked fish is also a special treat
40 locals recommend
Chatham Village Market
20 Queen Anne RdMy favorite small market ( CVS is next door). Super fresh seafood and sushi. The smoked fish is also a special treat
It is tiny, but a wonderful place to browse any time of year and you always find something interesting
32 locals recommend
The Brewster Book Store
2648 Main StIt is tiny, but a wonderful place to browse any time of year and you always find something interesting
Creative Arts Center In Chatham
154 Crowell RdLook for seasonal shows and sales all year long
Parnassus is a wonder! Explore hundreds of cheap used books in the outdoor gallery- any time of day or night! Explore new and used books in this wonderful old building or place an order for something specific. Great advice is always available
Parnassus Book Services
Parnassus is a wonder! Explore hundreds of cheap used books in the outdoor gallery- any time of day or night! Explore new and used books in this wonderful old building or place an order for something specific. Great advice is always available
Sightseeing
Beautiful location on Rock Harbor. Take abt out of the chapel - with its Italian tile baptismal font and lovely artwork. Take in a concert or evemaong and do t forget to visit the bookstore
Community of Jesus
5 Bay View DrBeautiful location on Rock Harbor. Take abt out of the chapel - with its Italian tile baptismal font and lovely artwork. Take in a concert or evemaong and do t forget to visit the bookstore
The visitor center is worth a visit for the incredible view out the back windows, the head of some
Wonderful trails including one that goes to the beach along marshy walkways and boardwalks, great informational maps and brochures and a film on the seashore.
97 locals recommend
Cape Cod National Seashore Salt Pond Visitor Center
50 Nauset RdThe visitor center is worth a visit for the incredible view out the back windows, the head of some
Wonderful trails including one that goes to the beach along marshy walkways and boardwalks, great informational maps and brochures and a film on the seashore.
Bass River
A beautiful inland waterway to see, kayak, fish and swim
Chatham Lighthouse
37 Main StEasy walk from downtown, great viewing area
Edward Gorey House
8 Strawberry LnGreat little museum and gift shop - check open hours
The lunch and dinner trains are supposed to be super! Nice view of the canal
26 locals recommend
Cape Cod Central Railroad Depot
252 Main StThe lunch and dinner trains are supposed to be super! Nice view of the canal
Interesting to a point - lovely location on Ryders Cove - historical site - nerds will be ecstatic
16 locals recommend
Chatham Marconi Maritime Center
847 Orleans RdInteresting to a point - lovely location on Ryders Cove - historical site - nerds will be ecstatic
For those interesting in holistic, heath places. My foster son loves this kind of thing.
Oceanair Himalayan Salt Cave
34 Main StFor those interesting in holistic, heath places. My foster son loves this kind of thing.
A great place to start your exploration of Ptowns art scene
55 locals recommend
Provincetown Art Association and Museum
460 Commercial StA great place to start your exploration of Ptowns art scene
Entertainment with food
Great art (films) house with Pizza Shark in the lobby! Small seating area. Rainy or cold day - No Problem!
Chatham Orpheum Theater
637 Main StCity advice
Getting around
Great scenic drive Rt 28 Orleans to Chatham
There is a lovely scenic drive on Rt 28 between Orleans and Chatham which takes you by Jackknife Beach and lovely Scenic coves. The most scenic parts are between Pleasant Bay Rd and the lighthouse in Chatham.
Customs and culture
Stony Brook School Pickleball Court
There is a pickleball court at the Stony Brook School in Brewster.
Getting around
Get Outside Cape Cod
Blog by Lissy Perna - advice on outdoor spots all over the Cape
Customs and culture
Whale watching and fishing cruises
Rock Harbor, Hyannis and Provincetown are all good places to explore Whale watches and fishing cruises Explore with your internet browser
Getting around
eTourChatham
Smartphone tour of Chatham