Rockport

Day Trips

Make the most of your day with our curated plans, packed with Rockport's hidden gems and unique experiences!

day 1
Arrival and Exploring the Waterfront
morning
:

Arrive in Rockport and settle into your charming accommodation. Start your day with a leisurely breakfast at a local café, where you can enjoy freshly baked pastries and coffee while soaking in the harbor views. After breakfast, take a stroll along the waterfront, admiring the boats and the picturesque scenery.

afternoon
:

Spend the afternoon visiting the Rockport Art Association and enjoying the local galleries showcasing beautiful coastal art. Head to Bearskin Neck, where you can explore unique shops and boutiques, offering everything from handmade crafts to nautical souvenirs. Don't miss the chance to grab a lobster roll from a nearby eatery for lunch!

evening
:

As the sun sets, find a cozy seafood restaurant where you can indulge in a fresh catch of the day. Enjoy a delightful dinner while listening to live music or the soothing sound of waves against the shore. End your evening with a sunset walk along the beach, taking in the breathtaking views of the Atlantic.

day 2
Hiking and Coastal Views
morning
:

Start your day early with a hearty breakfast before heading out to the nearby Halibut Point State Park. Lace up your hiking boots and explore the park's scenic trails, taking in stunning panoramic views of the coastline and rocky shores. Make sure to bring your camera to capture the unique landscape and wildlife along the way.

afternoon
:

After your hike, unwind with a picnic lunch at one of the park’s scenic overlooks. Then, head down to the sandy shores of Front Beach for some relaxation or water activities, like paddleboarding or kayaking. The afternoon sun provides the perfect backdrop for soaking up the casual beach atmosphere.

evening
:

As evening approaches, consider visiting a local vineyard for a relaxing wine tasting experience. Savor delightful local wines on their terrace, enjoying friendly conversation amid beautiful vineyard vistas. Afterward, find a laid-back spot for dinner, perhaps sampling some fresh seafood paired with a local craft beer.

day 3
Historic Sights and Shopping
morning
:

After breakfast, embark on a historical journey by visiting the famous Motif No. 1, a red fishing shack that's one of the most photographed buildings in America. Learn about Rockport’s fishing history and its significance to artists over the years. Don’t forget to capture a few photos of this iconic site!

afternoon
:

Continue your exploration with a trip to the Rockport Historical Society Museum, where you can dive into the rich heritage and maritime history of the town. Once finished, spend the afternoon browsing the arts and crafts shops on Dock Square, where you can find unique handmade items and local artworks. Grab a light lunch at one of the charming cafés offering local delicacies.

evening
:

For dinner, treat yourself to a nice meal at an upscale restaurant overlooking the harbor. Enjoy fresh local ingredients crafted into delicious dishes while soaking in the charming ambiance. Wind down your evening with a night stroll through the village, appreciating the welcoming lights and vibrant nightlife.

day 4
Whale Watching Adventure
morning
:

Enjoy a hearty breakfast at your hotel, then prepare for an exciting day of whale watching. Join a guided boat tour that departs from Rockport harbor, set against the stunning backdrop of the Atlantic Ocean. Keep your eyes peeled for humpback and minke whales as you venture into their natural habitat.

afternoon
:

Savor a packed lunch on board while being dazzled by the sight of these magnificent creatures jumping and breaching the surface. Your tour guide will provide fascinating insights into whale behavior and conservation efforts. Return to shore in the afternoon, filled with thrilling stories to tell.

evening
:

After the adventure, dine at a local restaurant known for its fresh seafood, reflecting on the day's experiences with your travel companions. Choose a spot with outdoor seating to enjoy the fresh ocean breeze. Conclude the evening with a calming walk along the rocky coastline, listening to the sounds of the waves beneath a starlit sky.

day 5
Arts and Culture Exploration
morning
:

Start your day with breakfast at a beloved local diner known for its hearty morning meals and friendly service. Afterward, visit the Shalin Liu Performance Center to appreciate its impressive architecture before seeing if any concerts or events are scheduled during your stay. Engage with the vibrant arts community by visiting local artists’ studios or joining a workshop.

afternoon
:

Have lunch at a café, where you can continue to immerse yourself in the artistic atmosphere of Rockport. In the afternoon, take a leisurely stroll through the many art galleries that line the streets, showcasing exclusive works that reflect the town's natural beauty. Speak with local artists when possible to gain deeper insight into their creative processes.

evening
:

For dinner, attend a live performance at the Shalin Liu, where an eclectic array of music and theatre can be enjoyed. Indulge in dinner before the show, perhaps choosing an establishment that focuses on farm-to-table ingredients. Spend the night reveling in the cultural heartbeat of Rockport, leaving with cherished memories.

day 6
Beach Day and Ocean Fun
morning
:

Prepare for a relaxing beach day with a fulfilling breakfast at a nearby café. Head to the popular Old Garden Beach, where you can set up your beach gear and enjoy a morning of sunbathing and swimming in the refreshing Atlantic waters. Collect seashells and enjoy the tranquil ambiance of the seaside.

afternoon
:

Take part in beach games or rent a bike to explore the nearby coastal paths for a fun afternoon adventure. Consider having a beachside picnic with some delicious snacks and beverages from a local market. If you're feeling adventurous, try water activities like snorkeling or paddleboarding to explore the marine life.

evening
:

As the day comes to a close, have dinner at a beachside seafood shack, enjoying the catch of the day. Share stories with fellow beachgoers and relish the post-sunset sky as it transitions into night. Conclude your beach day with a bonfire if allowed, sharing s'mores and laughter under the stars.

day 7
Local Markets and East End Delights
morning
:

Start your day with a visit to the local farmer's market, where you can enjoy fresh produce and local delicacies from friendly vendors. Sample delicious baked goods and homemade jams as you mingle with local residents. Make sure to pick up some treats for a picnic later in the day.

afternoon
:

Afterward, take a scenic drive to the east end of Rockport, where you can explore more quaint shops and galleries. Stop at a charming café for lunch and enjoy al fresco dining while relishing the bustling atmosphere. Spend the afternoon visiting the nearby beaches or enjoy a scenic walk along the rocky bluffs.

evening
:

For your final evening in Rockport, enjoy a farewell dinner at a rooftop restaurant that offers stunning sunset views over the harbor. Sip on a signature cocktail as you reflect on the amazing experiences you've had throughout your stay. Celebrate your trip by participating in a local event or festival if one is happening, engaging in the local spirit.

day 8
Departure Day and Farewell
morning
:

Have a leisurely breakfast at your hotel, savoring your final moments in this charming coastal town. Take the opportunity for one last stroll along the scenic seafront to capture any final photos. Gather souvenirs from local shops to bring a piece of Rockport home with you.

afternoon
:

Prepare to check out and reflect on the wonderful experiences of your stay, perhaps stopping by a favorite café for a light lunch. Allow some time for additional exploration of any spots you may have missed and soak in the coastal beauty one last time. Make your way to the car, feeling rejuvenated and inspired.

evening
:

As you depart Rockport, take in the stunning views of the coastline one last time, holding onto the memories created during your visit. Consider noting down your favorite moments on the drive home, keeping the joyful experiences close to your heart. Look forward to hopefully returning to this cozy seaside town in the future!

Discover Rockport

Read more in our Rockport 2025 Travel Guide.

Rockport Travel Guide