We often think we need an expensive vacation or a complicated itinerary to make summer feel special, but some of my favorite days have been much simpler than that.
A beautiful walk, a picnic packed from home, an interesting historic site, a live show, or a great seafood lunch can turn an ordinary day into a memory. These are ten places in Massachusetts and nearby New England that I’ve personally visited and enjoyed.
Some are well known, while others may be places you haven’t considered. Either way, I hope this list inspires you to take a day off, grab someone you love, and explore somewhere new—or rediscover somewhere you haven’t visited in a while.
1. See Grease and Explore Portsmouth, New Hampshire
I just visited Portsmouth this past weekend to see Grease at The Seacoast Repertory Theatre, better known as The Rep, and it was such a fun and nostalgic experience.
When I was a kid, I was completely obsessed with the movie Grease. I watched it so many times that I could practically recite the entire movie. Certain members of my family—who shall remain nameless—would sometimes hide the VHS tape because they were so sick of hearing it…
Seeing the story performed live brought all of those memories back. The show was fun, energetic, and entertaining, and I think it would be enjoyable even for someone who wasn’t quite as obsessed with the movie as I was.
Grease is playing at The Seacoast Rep this summer. You can view the current performance schedule and purchase tickets through the official Seacoast Rep website. The Rep is playing Grease until August 16, 2026. Purchase tickets here.
The show alone is worth the trip, but Portsmouth has so much more to offer. The downtown area is very walkable, with plenty of boutiques, small shops, restaurants, historic buildings, and beautiful views of the Piscataqua River and harbor. You can walk around without much of a plan, browse the stores, stop for coffee or dessert, and choose from several restaurants overlooking the water and boats. There are also narrated harbor cruises, sunset cruises, and evening cruises available if you want to add something extra to the day.
2. Pack a Picnic for Halibut Point State Park
Halibut Point State Park in Rockport is a place I have visited many times, and it never gets old.
It is perfect for anyone who wants to spend a beautiful day outside without needing an elaborate plan. There are walking trails, dramatic quarry views, rocky coastal scenery, and gorgeous views of the ocean.
The views are amazing, there are so many pretty places to stop and take pictures, and plenty to explore without the day feeling overly planned or rushed. You can walk around, take in the rocky coastline, and just enjoy being somewhere beautiful.
For me, being near the ocean always helps reset my soul, and Halibut Point is one of those places where you can slow down, breathe, and leave feeling better than when you arrived.
I would definitely bring lunch and make a picnic out of it. There are picnic areas and restrooms, so you can stay for a few hours and really enjoy the day. Bring plenty of water, wear comfortable shoes, and do not forget sunscreen.
This is more of a walking, exploring, sightseeing, and picnic destination than a swimming spot. Dogs are welcome too, as long as they are kept on a leash- or, if your dogs are as spoiled as mine were, they can be pushed around in a dog stroller or carried in a dog backpack! Yes that’s really me in this picture with Tyson in tote. 😹
3. Amethyst Brook and the Norwottuck Rail Trail
One of my favorite Western Massachusetts outings combines two beautiful places: Amethyst Brook Conservation Area and the Norwottuck Rail Trail.
Amethyst Brook is one of those places where you can immediately slow down and appreciate nature. The brook is beautiful, and the area feels peaceful and restorative. You can keep the walk relatively easy and flat near the brook, or explore some of the connecting trails if you want something longer.
After spending some time there, we usually make our way over to the Norwottuck Rail Trail. These are two separate locations, but they work nicely as parts of the same Western Massachusetts day.
The Norwottuck Rail Trail is a level, paved route that travels through Amherst, Hadley, Northampton, and Belchertown. One of its most memorable features is the large bridge crossing the Connecticut River between Hadley and Northampton. It is a wonderful place to walk, bike, get plenty of steps, and take in the surrounding landscape
You can pack a picnic or stop somewhere for lunch. Amherst and Northampton also have a variety of restaurants, thrift shops, bookstores, and small businesses to browse, so it is easy to turn the walks into full day.
Read more about Amethyst Brook Conservation Area and the Norwottuck Rail Trail before planning your
visit.
4. Louisa May Alcott’s Orchard House and Authors Ridge
Louisa May Alcott’s Orchard House in Concord is a place that means a lot to me. I grew up learning about Louisa May Alcott and loving Little Women. I even did a school book report on her when I was young. I first visited Orchard House as a child with my mom and dad, and years later, I returned as an adult with my nieces. It was such a fun and special day for me, and I hope it is one they will remember too.
Orchard House is where Louisa May Alcott wrote and set Little Women. The tour gives visitors a closer look at the Alcott family, their home, their beliefs, their creativity, and their unusual way of looking at the world.
Louisa was truly a woman before her time. Her determination, independence, writing career, and devotion to her family made a lasting impression on me when I was young. The stories of the entire Alcott family are fascinating, and I highly recommend taking the guided tour.
You can check current tour information and purchase tickets through the official Orchard House website. After the tour, take the time to visit Authors Ridge inside Sleepy Hollow Cemetery. Louisa May Alcott, Ralph Waldo Emerson, Henry David Thoreau, and Nathaniel Hawthorne are all buried in this area. Visitors often leave pencils, notes, and small tributes near the authors’ graves. It is quiet, beautiful, and moving to see how many people still feel connected to their work. Afterward, walk around downtown Concord and stop for lunch or dinner. The Concord’s Colonial Inn is one historic option if you want to make the day feel even more special.
5. A Girls’ Day at Pickity Place
I am sure many people have heard of Pickity Place, but it is also one of those places we sometimes forget about because it has been around for so long.
Located in Mason, New Hampshire, Pickity Place makes such a cute girls’ day out. I enjoy visiting with the ladies in my family, and it would also make a lovely birthday outing, mother-daughter day, or gift for someone special.
The atmosphere feels nostalgic and old-fashioned, and part of the fun is seeing what will be served. The menu changes regularly, so every visit can feel a little different. After lunch, take time to explore the gardens, greenhouse, and gift shop. The shop carries herbal blends, spices, loose-leaf teas, beverage mixes, dip mixes, and gifts. I always enjoy looking through everything
and there is a powdered beverage mix I like to bring home and make either hot or iced.
Dining reservations are needed and are made by phone. You can view menus, hours, and shopping information through the Pickity Place website.
It is not an action-packed day, and that is exactly what makes it nice. It is a chance to slow down, enjoy good food, browse the shop, and spend time with people you love.
6. Follow the Salem Heritage Trail and Eat at Finz
Anyone who knows me knows how much I love Halloween, and Salem has been a place I have visited for years.
Oddly enough, it almost feels like a home away from home. I cannot completely explain it, but I love the history, the atmosphere, the old buildings, the shops, and the excitement people bring with them when they visit. One of my favorite ways to explore Salem is by following the Salem Heritage Trail instead of walking around without a plan. The trail connects more than 400 years of the city’s history and leads you past historic locations, stores, restaurants, and attractions. You can keep the route on your phone while you walk.
One of my favorite places to stop is the Ropes Mansion and Garden. The exterior of the mansion was used as Allison’s house in Hocus Pocus, but the garden behind it is an attraction all by itself. It is a beautiful, peaceful place to sit for a while.
You can also visit The Witch House, the former home of Judge Jonathan Corwin and one of the few remaining structures with direct ties to the Salem witch trials. Other fun stops include the Bewitched statue, the Salem Witch Trials Memorial, and the Old Burying Point.
My favorite place to eat in Salem is Finz Seafood & Grill at Pickering Wharf. It sits overlooking Salem Harbor and offers seafood, lobster, sushi, and waterfront dining. There are also plenty of small shops around the wharf to browse before or after eating.
Salem becomes extremely crowded during the Halloween season, so be prepared for that or consider going earlier in the year.
Salem is commemorating its 400th anniversary through the Salem 400+ initiative, with special events and exhibits throughout 2026. So it’ll be an exciting time to visit but also BUSY!
7. A Simple Evening in Exeter, New Hampshire
Exeter is a good option for anyone looking for a quieter, simple New Hampshire outing. The downtown area has historic buildings, shops, restaurants, and views of the Squamscott River. Start by walking along Water Street and browsing some of the local businesses. Water Street Bookstore is an independent bookstore located in the heart of downtown and is a nice place
to spend time browsing. From there, take a walk through Swasey Parkway, which follows the river and has trees, benches, and space to sit and enjoy the view. You can also walk through the historic Front Street area, see the town bandstand, and explore the surroundings near Phillips Exeter Academy. For dinner, Vino e Vivo is an intimate restaurant and wine bar on Water Street that could be a nice choice for a relaxed date night or evening with friends.
Exeter is not a destination where you need a packed itinerary. It is better suited to walking, browsing, having dinner, and enjoying a peaceful New England evening.
8. Spend a Day at Wingaersheek Beach
Wingaersheek Beach in Gloucester is one of the most beautiful beaches I have ever seen—and I have seen a lot of beaches! The pale sand, clear shallow water, rocks, and wide tidal flats make it feel completely different from many other Massachusetts beaches. At low tide, you can walk far out across the sand and explore the surrounding area. There really is not much more I need to say about it. It is simply breathtaking, and I think everyone who lives in Massachusetts should try to see it at least once. Pack a picnic, bring water, wear sunscreen, and spend the day enjoying the beach. You could also stop for seafood afterward in Gloucester.
One important thing to know is that nonresident parking reservations are required during the main summer season. Check current parking details and reserve ahead through the City of Gloucester beach information
page. Parking is limited, so this is one outing that requires some advance planning.
9. Try an Immersive Art Experience
A while back, I attended the immersive Van Gogh exhibition with my dad, and I thought it was incredible. It was such a different way of experiencing art. Instead of simply viewing paintings on a wall, visitors were surrounded by projections, music, movement, color, and images inspired by Van Gogh’s work.
That particular Boston exhibition has ended, but it inspired me to look for other immersive experiences. One current option is WNDR Museum Boston, an interactive art experience in Downtown Crossing with immersive installations involving light, sound, reflections, technology, and audience participation. Check the website for current exhibits, ticket prices, and availability.
I have not tried WNDR yet, but it is something I would like to experience. I will report back if I go, and please let me know if you visit before I do!
10. Iggy’s and Rocky Point State Park in Rhode Island
Iggy’s Doughboys and Chowder House is such a fun Rhode Island outing.
The Warwick location is on Oakland Beach, and it has that casual, classic New England summertime feeling. You can order clam cakes, chowder, seafood, and, of course, doughboys, then eat near the water.
Iggy’s has locations in Warwick and Narragansett. You can check menus and locations through the Iggy’s website.
To make the drive feel even more worthwhile, pair it with a visit to Rocky Point State Park, which is also in Warwick. Rocky Point was once a beloved amusement park and entertainment destination. Today, the property includes public waterfront land, trails, open spaces, and reminders of its long history. It is simple, casual, nostalgic, and very New England.
Start Planning Your Next Day Out
A memorable day does not always require a flight, a hotel, or months of planning.
Sometimes it is a picnic overlooking the ocean, a walk across a bridge, a historic house, a live show, a beautiful garden, or seafood eaten near the water.
The important thing is making the time to go.
I hope you enjoyed the read. Please comment below if you’ve ever been to any of these locations, or if you have other recommendations for day trips in or near Massachusetts.
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