Cape Ann Guidebook
Neighborhoods
aka Downtown Rockport, or Bearskin Neck, this is a leisurely 15-minute walk from the house. You will want to leave the car behind on weekends and on busy days to avoid parking.
Oceanfront shops featuring art, gifts and souvenirs. Snacks and restaurants also available.
34 residents recomanen
Motif #1
Bradley Wharfaka Downtown Rockport, or Bearskin Neck, this is a leisurely 15-minute walk from the house. You will want to leave the car behind on weekends and on busy days to avoid parking.
Oceanfront shops featuring art, gifts and souvenirs. Snacks and restaurants also available.
Sister-town Gloucester is worth a visit to walk along the waterfront, see the local specialty shops on Main Street, and enjoy excellent dining options.
Spend an afternoon here, or combine with the Cape Ann Museum, harbor boat tours, or whale watching for a fun day.
Gloucester has a rich history as the oldest operating fishing port in the country. It is also home to a vibrant Sicilian community.
10 residents recomanen
Gloucester HarborWalk
9 Dale AvenueSister-town Gloucester is worth a visit to walk along the waterfront, see the local specialty shops on Main Street, and enjoy excellent dining options.
Spend an afternoon here, or combine with the Cape Ann Museum, harbor boat tours, or whale watching for a fun day.
Gloucester has a rich history as the oldest operating fishing port in the country. It is also home to a vibrant Sicilian community.
Visit the Antique Trail, only 20 minutes away in Essex and Ipswich. From vintage to colonial to fine European furniture, you are sure to find your own treasure to take home.
Check out the fried clams and microbrews while you're here.
Map available at:
https://www.visitessexma.com/shop
25 residents recomanen
Essex
Visit the Antique Trail, only 20 minutes away in Essex and Ipswich. From vintage to colonial to fine European furniture, you are sure to find your own treasure to take home.
Check out the fried clams and microbrews while you're here.
Map available at:
https://www.visitessexma.com/shop
Sightseeing
Learn about Cape Ann's historic fishing industry and Rockport's long-time inspiration for painters.
69 residents recomanen
Cape Ann Museum
27 Pleasant StLearn about Cape Ann's historic fishing industry and Rockport's long-time inspiration for painters.
See Rockport from a different angle- by sea! Kayak and bike rentals by the hour. Summers afford smooth seas, for which some dub our ocean "Lake Atlantic." There is still a thrill, none the less, when manning your own vessel in the open sea. Or stick to the harbors, up to you!
19 residents recomanen
North Shore Kayak Outdoor Center
9 Tuna WharfSee Rockport from a different angle- by sea! Kayak and bike rentals by the hour. Summers afford smooth seas, for which some dub our ocean "Lake Atlantic." There is still a thrill, none the less, when manning your own vessel in the open sea. Or stick to the harbors, up to you!
Outstanding and intimate concert hall featuring world-class performers with an unbeatable view. Enjoy a peaceful stroll from the house to this venue in the heart of town.
77 residents recomanen
Rockport Music-Shalin Liu Performance Center
37 Main StOutstanding and intimate concert hall featuring world-class performers with an unbeatable view. Enjoy a peaceful stroll from the house to this venue in the heart of town.
Restaurants
A sampling of our favorite bites.
Fresh seafood options at family-friendly prices (yes, it exists!) Located at Rockport's center and walking distance from your stay.
Call ahead on busy nights, as they can reach capacity.
26 residents recomanen
Roy Moore's Fish Shack Restaurant
21 Dock SquareFresh seafood options at family-friendly prices (yes, it exists!) Located at Rockport's center and walking distance from your stay.
Call ahead on busy nights, as they can reach capacity.
Lively restaurant with drinks and creative seafood dishes. A fun place with harbor views.
50 residents recomanen
Minglewood Harborside
25 Rogers StLively restaurant with drinks and creative seafood dishes. A fun place with harbor views.
Intimate dining and beautiful views featuring fresh seafood and other options. Also walking distance from your stay. Reservations required.
44 residents recomanen
My Place by the Sea
68 Bearskin NeckIntimate dining and beautiful views featuring fresh seafood and other options. Also walking distance from your stay. Reservations required.
Casual, artsy cafe with sandwiches, soups, beer and full bar and live music Friday nights at 7-9pm and weekends 12-2pm.
Check out their Facebook page, they have fun events all the time!
8 residents recomanen
Whale's Jaw Cafe
17 Railroad AvenueCasual, artsy cafe with sandwiches, soups, beer and full bar and live music Friday nights at 7-9pm and weekends 12-2pm.
Check out their Facebook page, they have fun events all the time!
*Next door Surfside Subs has GREAT pizzas, but can't add it as a separate listing on here!*
Just drive by and know the lines do not lie. The sizes are simply irresponsible. 24 flavors of soft serve. As the weather warms up, my mind keeps circling back to the the last frappe I had here, like some recurring phantom addiction.
frappe= "New English" for milk shake
8 residents recomanen
Long Beach Dairy Maid
147 Thatcher Rd*Next door Surfside Subs has GREAT pizzas, but can't add it as a separate listing on here!*
Just drive by and know the lines do not lie. The sizes are simply irresponsible. 24 flavors of soft serve. As the weather warms up, my mind keeps circling back to the the last frappe I had here, like some recurring phantom addiction.
frappe= "New English" for milk shake
Small restaurant with a global-inspired menu in downtown Gloucester.
"Everthing here is delicious!"
-Your hosts
25 residents recomanen
Passports
110 Main StSmall restaurant with a global-inspired menu in downtown Gloucester.
"Everthing here is delicious!"
-Your hosts
With seafood in all its wonderful forms, this place is a favorite for special meals. Also has nice views of the harbor.
31 residents recomanen
Seaport Grill
6 Rowe SquareWith seafood in all its wonderful forms, this place is a favorite for special meals. Also has nice views of the harbor.
Good seafood and a family-friendly setting has made this a landmark in Gloucester for almost 30 years. Seafood bib optional.
35 residents recomanen
Lobsta Land Restaurant
84 Causeway StGood seafood and a family-friendly setting has made this a landmark in Gloucester for almost 30 years. Seafood bib optional.
Landmark fried clams and lobster rolls in a casual setting. This is the best place for this New England specialty! Great Marsh Brewing is next door. And stop by one of the many antique shops on the way in Essex.
37 residents recomanen
Woodman's of Essex
119 Main StLandmark fried clams and lobster rolls in a casual setting. This is the best place for this New England specialty! Great Marsh Brewing is next door. And stop by one of the many antique shops on the way in Essex.
Hidden gem for fine dining on the Annisquam River. Open for dinner and brunch. The menu changes daily and the dishes are amazin.
10 residents recomanen
Talise
33 River RdHidden gem for fine dining on the Annisquam River. Open for dinner and brunch. The menu changes daily and the dishes are amazin.
Beachs
Some small, some big, these are our favorites and how to get there.
Sandy Long Beach in Gloucester is a local favorite! Parking is restricted to residents, so we recommend using a taxi. (Direct them to Cape Ann Motor Inn at 33 Rockport Rd, Gloucester, MA 01930)
10 residents recomanen
Long Beach Gloucester
44-30 Rockport RdSandy Long Beach in Gloucester is a local favorite! Parking is restricted to residents, so we recommend using a taxi. (Direct them to Cape Ann Motor Inn at 33 Rockport Rd, Gloucester, MA 01930)
Popular wide sandy beach between Rockport and Gloucester with lifeguards, restrooms, showers and concessions available 9am-5pm daily, gates open 8am-9pm.
Access:
Advanced parking reservations are required for $30/weekday per car, and $35/day weekend. *Reservations available ONLY via the Gloucester Yodel website up to 10 days in advance. Cash is not accepted at the gate. We highly advise to reserve early for weekends.
(search online for "Gloucester beach pass to purchase")
(updated 7/2022)
118 residents recomanen
Good Harbor Beach
Popular wide sandy beach between Rockport and Gloucester with lifeguards, restrooms, showers and concessions available 9am-5pm daily, gates open 8am-9pm.
Access:
Advanced parking reservations are required for $30/weekday per car, and $35/day weekend. *Reservations available ONLY via the Gloucester Yodel website up to 10 days in advance. Cash is not accepted at the gate. We highly advise to reserve early for weekends.
(search online for "Gloucester beach pass to purchase")
(updated 7/2022)
Small, sandy beach, a nice walk away! Adjacent to Rockport's shopping area. Come at low tide for the most real estate.
38 residents recomanen
Front Beach
Small, sandy beach, a nice walk away! Adjacent to Rockport's shopping area. Come at low tide for the most real estate.
Family-friendly beach with white sand, no waves and clear water in Gloucester along the Annisquam River and Ipswich Bay. During low tide the water retreats a half mile revealing sand bars, giant rocks and tidal pools, which are fun to explore for all ages.
Lifeguards, restrooms, showers and concessions are available 9am-5pm daily, gates open 8am-9pm.
Access:
Advanced parking reservations are required for $30/weekday per car, and $35/day weekend.
*Reservations available ONLY via the Gloucester Yodel website up to 10 days in advance. Cash is not accepted at the gate. We highly advise reserving early for weekends.
(search online for "Gloucester beach pass to purchase")
(updated 7/2022)
66 residents recomanen
Wingaersheek Beach
Family-friendly beach with white sand, no waves and clear water in Gloucester along the Annisquam River and Ipswich Bay. During low tide the water retreats a half mile revealing sand bars, giant rocks and tidal pools, which are fun to explore for all ages.
Lifeguards, restrooms, showers and concessions are available 9am-5pm daily, gates open 8am-9pm.
Access:
Advanced parking reservations are required for $30/weekday per car, and $35/day weekend.
*Reservations available ONLY via the Gloucester Yodel website up to 10 days in advance. Cash is not accepted at the gate. We highly advise reserving early for weekends.
(search online for "Gloucester beach pass to purchase")
(updated 7/2022)
Nature
Easy parking and wide dirt path to view an historic granite quarry and ocean overlook.
115 residents recomanen
Halibut Point State Park
Gott AvenueEasy parking and wide dirt path to view an historic granite quarry and ocean overlook.
Breweries
New England is home to many great microbrews, and this one is close by and has the relaxed fun vibe you'd hope for to enjoy a cold one.
9 residents recomanen
True North Ale Company
116 County RdNew England is home to many great microbrews, and this one is close by and has the relaxed fun vibe you'd hope for to enjoy a cold one.
Huge local mircobrew with a full restaurant and views of the marsh.
15 residents recomanen
Great Marsh Brewing Company
99 Main StHuge local mircobrew with a full restaurant and views of the marsh.
Food Scene
Which is the best Italian bakery in town? You'll have to come try to find out. Features expresso and Gelato.
14 residents recomanen
Caffe Sicilia
40 Main StWhich is the best Italian bakery in town? You'll have to come try to find out. Features expresso and Gelato.
A taste of Italian-America, backed by a strong local Sicilian community. Baked goods, sandwiches, and quick pizza slices. To-go only, but there are lots of places to enjoy the scenery near-by.
36 residents recomanen
Virgilio's Italian Bakery
29 Main StA taste of Italian-America, backed by a strong local Sicilian community. Baked goods, sandwiches, and quick pizza slices. To-go only, but there are lots of places to enjoy the scenery near-by.
Great flavors and quality. Call ahead to order from this local cake shop, or stop by for treats to-go.
9 residents recomanen
Cake Ann
63 Rogers StreetGreat flavors and quality. Call ahead to order from this local cake shop, or stop by for treats to-go.
Old World shop with wine, cheese, chocolate and other goodies. Stop for a fun treat and knowledgeable, passionate owners.
8 residents recomanen
The Cave
44 Main StOld World shop with wine, cheese, chocolate and other goodies. Stop for a fun treat and knowledgeable, passionate owners.
This is a fish market, not restaurant! Come here if you want to cook your meal yourself. It's all super fresh and will knock your socks off.
7 residents recomanen
Turner's Seafood Market & Fish n Chips Shoppe
4 Smith StThis is a fish market, not restaurant! Come here if you want to cook your meal yourself. It's all super fresh and will knock your socks off.