Photo by Muffy Aldrich
The Modern Guide to The Thing Before Preppy

Wednesday, September 13, 2023

Between Gloucester, Newburyport and Points North to the New Hampshire Line.

 A reader question:

Hopefully we will be heading to salt water Massachusetts next month.  Since this community is well informed and helpful about all things in that part of the world, any suggestions about what not to miss between Gloucester, Newburyport and points north to the New Hampshire line?  Any particular favorite drive or local restaurants the tourists overlook?   It was great exploring Gloucester south to Marblehead last year so we wanted  to do something different this year.   Thanks for any and all suggestions.  Thank you!

23 comments:

  1. Begin in Gloucester. Drive approximately 100 yards. Get out. Enjoy the best place in the world. Get back in the car, drive 100 yards…you get where this is going, right?

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  2. If you want quality time at an isolated part of the shoreline near Newburyport, Sandy Point State Reservation at the southern end of Plum Island. Not much parking if you’re going on a weekend. If you’re the kind of person who likes the mansions in Newport, RI, Castle Hill on the Crane Estate in Ipswich - $ to get in and tour, but it’s a nice spot with interesting history. You could also cross the NH line and spend a day in Portsmouth (where I used to live) ride a bike around Newcastle, decent restaurants, good brewery there, there are boats that go out along the coast if you’re into that.

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  3. Visit Crane Beach and the Crane Estate in Ipswich and grab lunch at Woodman's of Essex (its much quieter in the fall). Sandy Point is a terrific spot on Plum Island and Maudsley State Park in Newburyport is a hidden gem. Lowell's Boat Shop, across the river from the park is a nice take as well.

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    1. Better yet, if you get the opportunity, check out the Crane Estate. The beach gets swamped and parking can be a nightmare; if you're a Trustees member, the estate's the way to go for the views and for the old money feel of the estate itself.

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    2. Woodman's is a tourist trap. Locals know to go to either J.T. Farnhams or Essex Seafood for your fried clam fix. But, if you'll be in Ipswich, the Clam Box is your best bet. After walking the dunes and beach at Crane's, I recommend a good burger and beer at the Choate Bridge Pub in downtown Ipswich.

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    3. Anon 1:21 - respectfully disagree. Locals know to skip the weekends and take advantage of the midweek specials. The food is excellent and the Woodmans are great! Farnham's and Essex are good as well and the steak tips at the Choate Bridge are amazing.

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  4. Some other beaches: Good Harbor Beach and Wingaersheek Beach. No entrance fee or resident sticker req'd after Labor Day. Did you get to Rockport harbor on Cape Ann last year? The Cape Ann Museum?

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  5. If you make it by October 16th, the Cape Ann Museum has an Edward Hopper exhibit. If you side track a bit to Rockport, Halibut Point State Park is awesome and you can take in the little section of Gloucester called Annisquam to rejoin Rt 127. You can walk out on the jetty at Gloucester's Eastern point. Oldies Marketplace in Newburyport is a great (huge) junk shop. Portsmouth's Strawberry Bank is fabulous. Good food in Newburyport: The Paddle Inn, The Black Cow and Sea Level. Good food in Gloucester: Tonno and The Beauport. The Clipper City Rail Trail is good for biking or walking. The Essex Coastal Scenic byway has lots of good info: https://coastalbyway.org/

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    1. Cape Ann museum is a must. And don't forget to visit Bearskin Neck in Rockport.

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  6. A drive around the perimeter of Cape Anne taking in vistas of the sea near Thacher Island Light House (once part of the famous "Twin Lights") a stop to visit the charms of Smith Cove (artists' colony south of Gloucester), Rockport and Annisquam (large fleet of Samuel Crocker boats), a visit to Coggeswell Grant (folk art in a charming 17th century house), and the Parson Capen House (a very old seventeenth-century house) in Topsfield, maybe take in the Topsfield Fair. Those are just a few ideas, there are many more..

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    1. Perimeter route around Cape Ann is Rt. 127. Start in Beverly, and follow it through Manchester-by-the-Sea, Magnolia, Gloucester, and Rockport. You can jump back on 128 south at the rotary at the end.

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  7. Rockport is a very pretty town and art colony. Essex is good for antiqueing.

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  8. In Essex take the Essex River Cruise…peaceful and informative. Stop at Farnhams for lunch. The Cape Ann Museum in Gloucester has a wonderful Edward Hopper exhibit on until Mid October. Lunch on the deck of the Beauport Hotel is an indulgent treat. The $10 (good for the whole day) water taxi takes you all around Gloucester’s vast harbor. Newburyport is a shopper’s dream. Locals love The Grog which serves one of the best burgers on the Northshore. Take a ride out to Plum Island. Bob Lobster for lobster rolls. You won’t run out of things to do!

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  9. I would second a few of the recommendations here, but add that the Crane Estate tops the beach in terms of aesthetic and views of the shoreline. Ipswich, which you'll have to drive through to get from Gloucester to Newburyport still feels like an old school New England town in a way that much of the North Shore doesn't anymore. Patsy's recommendation of Halibut point state park is also spot on; there's not much else like it.

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    1. The Grog is great. Long live The Grog.

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  11. A story about the Crane estate: The parents of a boarding school classmate threw a graduation party for the class there. One of my classmates brought an interesting pretty girl and at some point during the evening she and I started to hit it off. She lived not far from my home and I had my car so she suggested she claim she was ill and told her date that 'since I'd be driving past her hometown I could conveniently drop her off'. I kind of felt bad for her date, a guy I didn't know well. When we got to her house she cooked up a great midnight breakfast and we got to know each other pretty well....

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  12. Absolutely check out Cogswell's Grant. Beautiful old house and spectacular collection. Crane Estate is certainly a grand place to tour. My grandmother was a Crane. A Dawchestah cousin... LOL! Cheers!

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  13. Check out the Rusty Can in Byfield. Amazing BBQ. Bring a book and be prepared to wait a bit as the line gets long. Better, do takeout and bring it to the beach. Crane is super if you are off season and don't have to register online to park even as a member (venting!!!!!) and downtown Ipswich is adorable with cute antique shops and townie spots. 1A in Rowley is dispensary row (3!) and the Mill River Winery in the same stretch is the perfect place to get your vice on, if your are so inclined, and as an alternative to the excellent breweries popping up all over. Do head up to Portsmouth for popovers at Popover On The Square. Yum. AVOID the sunflowers on Scotland Road in Newbury. It used to be cool and fun and "Oh look!" when driving by but now it is Zoobury traffic cluster of folks in matching denim and white t-shirts and circle lights taking selfies for holiday cards and I think they even charge folks now. Don't do it, though it sounds like your trip may be past the time. Finally, do a little bit of hiking on the Appleton Farms trails. And, get some apple cider donuts at Russell Orchard on Argilla on way back from Crane Beach. Oh, and most importantly, bring waterproof boots! We have never had so much rain as in the past few months. I keep thinking I moved to Seattle!

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  14. Agawam Diner, featured prominently in Robert Parker's 'Spencer" private eye series of books. The waitstaff is as humorously loud, intolerant and snarky as Durgin Park's used to be.

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    1. My father went school in Cambridge and for his 70th took us to Durgin... hilarious.

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  15. If you're up for a hike, seek out Dogtown in Gloucester. Try to find all the Babson boulders!

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  16. Thank you for all the wonderful suggestions. We're so hoping for cool, clear fall days but a rainy day would be great to do some of the indoor activities. Now, if we could just extend our hotel stay a little longer!

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