Beginner's Guide to Rockport, MA

motif #1

Most Often Painted Building in America

ROCKPORT, MA

Just a little over an hour outside of Boston you'll be happy to find the quintessential little seaside getaway town of Rockport, MA. Whether you're staying here for the day or a week, your bucket list of items to see and do will never run short; it couldn't be more charming. Honestly, while you're there you'll probably find yourself perusing local Real Estate to stay for good!If you want to get the most out of your trip, work some of these into your itinerary and you're bound for a good time!Here's the categories we'll cover:

Crave worthy Food/Drink
Outdoor Experiences
Local Vibe (culture/history)
Where to Stay & How to Relax
Side Trips

I'd encourage you to use these suggestions like menu items. Craft your ideal trip based on who you're traveling with and your interests! Comment below with your favorites or if you've been to any of the places. Let's get started!

Our Trip:

Length of Trip: Four Days, 3 nights
Home Base: VRBO about 1 mile up the street from Bearskin Neck where all the shopping and activity is.

Munch & Sip, enjoy the good life.

I'll add a little caveat to this part. We went during COVID-19 so there weren't many restaurants open, many just for take-out. We spent three nights here and chose to eat out 2/3 nights and grill at our VRBO the other night. So, this is not a full list but the restaurants we found quite satisfying!

Bean & Leaf Cafe, cafe by the sea. The Best Coffee Run in the Morning is also an ice cream store. Well, they're right next to each other and both deliver a top-notch experience and product. I craved the drip coffee from here (black, nothing added) and my wife was obsessed with their macchiatos (espresso coffee drink with a small amount of milk, usually foamed). For someone who studied abroad in Italy for a year, that's saying a lot. We would walk down each morning to get some exercise and grab our caffeine fix; just perfect. The Ice Cream Store had some long lines and is well worth the wait. You see the picture, wouldn't you agree?

The Lobster Pool, A cozy red shack with indoor & outdoor seating, it's settled right in front of Ipswich Bay so you know the views are stellar. They boast Ocean Fresh Seafood Made-to-Order! They are BYOB, so if you want to imbibe, bring your own. Their tank of fresh live lobsters is a spectacle. If you order one, they'll take it out of the tank and cook it right there on the spot! Between three adults, we opted for two meals to share because of the large portions. Meal One was the Fisherman's Plate: fried shrimp, scallops, clams, and haddock bites (comes with fries & coleslaw). Other meal: The Rockporter (greens, apples, walnuts, dried cranberries, blue cheese).

Oceanfront dining near overlooking Cape Ann

Blue Lobster Grille, Located right before you step onto Bearskin Neck this American style Seafood restaurant has something for everyone. They had a nice selection of grilled, fried and otherwise prepared menu items. I ordered and loved the Blue Cheese Scallops. It was a special that evening, so I can't guarantee it'll be there when you go, but let me tell you-SCRUMPTIOUS. It is served with 6-7 huge sea scallops, covered with blue cheese (sounds odd, I know, but stick with me) grated Parmesan cheese and bread crumbs then baked. The quality and size of the scallops showed me they knew what they were doing. The entire portion was a really nice size, so much so you could definitely share. The other meal we ordered was the Seafood Risotto-also great. This was a nice size portion and packed with seafood! All in all, very happy we stopped here. They have great outdoor seating in the back of the restaurant (closed off when we were there) but also tables out front on the sidewalk (great for people watching).

Our BEST idea the entire visit:

We grabbed our meals to-go and drove to Cape Hedge Beach. Threw down the beach chairs and enjoyed our meals truly ocean front.

Feather & Wedge is a great place to head to if you want a little more upscale experience. Their menu offers some local seafood favorites and some staples that will surely satisfy. They’re open for indoor and outdoor dining, have take-out and will deliver if you prefer. We sat outside overlooking Bearskin Neck and had a magical evening. We shared a few fresh and scrumptious plates: The F&W shrimp and leek egg rolls, Caprese Salad | heirloom tomatoes, buratta, basil , Federico’s roasted chicken | mashed potatoes, green beans, lemon pan sauce. Each dish tasted amazing with a glass of Sauvignon Blanc.

Exercise, get a little sweat going.

Scenic walk.

A stone's throw from The Lobster Pool is Halibut State Park for some light hiking with a scenic overlook, as recommended by locals. This would be a good place to go for a walk then grab some lunch/dinner at The Lobster Pool. Parking is $5 for Massachusettes plates and $20 for non-Massachusetts plates. Dogs are welcome, on a leash. Check the updates on COVID from the Parks department before heading out.

Harder Hike with History.

Visit Dogtown Loop Hiking Trail, the town with an eerie history. Strewn throughout are boulders with carved inspirational sayings; quite a spectacle. It's about 6 miles in total and is a beautiful stretch of forest between Gloucester and Rockport; located about 15 min. from the heart of Rockport.

BYOB (Bring your own Bike) or rent them.

We brought ours, but you can rent right at the Addison Choate Hotel and have a great time. You could cover quite a bit of ground on a bicycle if you wanted to. Grab a coffee, see the view from the end of Bearskin Neck, ride to a nearby beach and relax. Really, the sky is the limit if you want to ditch the car for a day or don't feel like walking everywhere.

Local Vibe, take in history of town

One of the best parts of this place (and a lot of New England) is you'll notice as you walk around how many of the homes and buildings are historical homes, built back in the 18th century. Free Guided Walking Tours. Hosted by the Rockport Cultural District, they're 1 hour 15 min and it's free! Ends up being about 1.2 miles in total. Get to know a little bit more about one of America's oldest art colonies.

Beauport, the Sleeper-McCann House. In Gloucester, tour this historical home that is a National Historic Landmark. It was the summer home for one of America's first Interior Designers-so you know it's a spectacle! There's over 40 rooms to look at and no two of them are the same. Purchase advance tickets for $20/adult, $17/seniors, $8/students & children.

Where to Stay & How to Relax

Sometimes vacations are more exhausting than you plan. However, this little ocean town was serene and had such great vibes. I said to myself a few times while I was there, 'ahhh, this is the good life.' We chose to stay in a VRBO off of South Street on Eden Street that was a hop skip & a jump from the ocean. There's no beach access, but we could walk to some pretty fantastic large rocks to sit on and enjoy the morning sunrise. Stunning. If I were to go back here, I would choose to stay in or around this location again. Each morning, we woke up to walk our dogs, ride bikes and just have some peace-all along the ocean. There were other places to stay for rentals that looked fantastic as well, namely the Eden Pines Inn. She books up quickly, so plan ahead!

Another great option is the Addison Choate (referenced below surrounding bike rentals). I’ve done a full write-up about one of the cutest, most hip historical inn in Rockport. Check it out here.

Hands Down recommend this great view of the sunset: Plum Cove Beach.
We packed some wine and beach chairs and headed there after dinner. You're tucked in a little cove, so it's pretty quiet there.

Beaches

We found solitude and peace at two more hard to get to beaches: Pebble Beach & Cape Hedge Beach. We found them first by bicycle and then later made our way back towards dinner time when we knew parking rules would be more lenient for non-residents. All depends how risky you want to be!

For a local view on best beaches (mine is listed on there, so you know it's good!), the Addison Choate hotel has a great post you should read if beaches are your JAM. If you wanted bikes and go beach hopping, this hotel does rent bikes for $15/hour that includes helmet & lock.

Favorite Shops

Lula's Pantry. Eclectic kitchen and home goods. Such a good vibe in here; a must visit. Sneak to the back and grab one of the best views of Motif #1 on their deck.

One Ocean One Love Shop. Small eco-friendly shop that was created passion to conserve and protect marine life. They have hand-printed surf-inspired clothing that's one of a kind and 5% of all One Ocean net profits are donated to keeping the oceans clean.

Wicked Peacock. Cozy and fun accessories boutique with many on-trend jewelry pieces and cute tunics and tops. Employees were very sweet and helpful-would definitely go back!

lula’s pantry

for all of your fun kitchen needs

Wandering

Crane Estate, Ipswich, MA. Located about 30 minutes down the coast to a stunning historical mansion that overlooks winding salt marshes and local beaches. The estate has marvelously manicured gardens that would woo even the blackest of green thumbs. Don't even get me started about the views. The sprawling lawn from the estate undulates right up to the ocean cliffs.

Newburyport. Another quintessential ocean town that's worth the 45-50 minute drive up the coast. There's quite a bit to do there as well and history to see/learn.

Plum Island Barrier Beach.While you're in Newburyport, if you want to enjoy the outdoors a great place to ride bikes for about an hour and see some cool animals. Also, lots of places to grab food afterwards.

Maudslay State Park. Another great place to enjoy the outdoors. It's located on an old estate and has a variety of different open field and forest trails. Parking rules apply, dogs are welcome.

back lawn at crane estate

just a tiny yard to mow, no big deal.

TRAVEL NOTE: Since many businesses and venues are adjusting their operations in response to COVID-19 health concerns, please contact them directly or check their websites before making travel plans