Senior Travel 2023

| 19 Jul 2023 | 12:39

Visit Pittsfield — The Heart of the Berkshires

Until Columbus Day weekend, 3:15pm on Fridays is a magic hour at the Moynihan Train Hall. It is the departure time for Amtrak’s Berkshire Flyer for a four-hour journey to Pittsfield, MA. The train travels along the scenic Hudson River to Albany and then ascends 1,500 feet on the 50-mile journey through the Berkshire Mountains to its terminus. The city, well-placed as the center of the Berkshire Region, offers many activities available to you within a stone’s throw from your downtown location.


On a recent Berkshire Flyer trip, ( we discovered there was much to learn about visiting here. Did you know that Pittsfield resident Herman Melville lived in Manhattan for most of his life? Who were the Shakers and what were their lives like? Want to hike to a prosaic pond that is 2,100 feet high - about the height of the Empire State Building and the USS Intrepid stacked together? There are many unique paths awaiting discovery.


After a good night’s sleep, what could be better than to take a short stroll on a Saturday morning to visit the local market? The teen-run outdoors Saturday Pittsfield Farmers Market is open from 9am to 1pm until mid-October, offering local fruits and vegetables, artisan crafts and more. Engage with the vendors and you will feel like a local within a few minutes.


Arrowhead, just south of Pittsfield, includes the grounds, house and barns of Manhattanite Herman Melville, who was born and died on our island. Berkshire County Historical Society’s stewardship of the 1780s farm estate seeks to restore the house to the era between 1850 and 1862, when Herman Melville owned it, and wrote Moby Dick while residing there. Guided house tours, grounds tours and the Melville Trail cover the scenic estate, which is in a woods and mountain-filled location. An informative briefing chronicles the rich details of Melville’s life. In the house you can see the desk (with a window overlooking the mountains) where he sat and wrote, and some of the rooms where his extended family lived.

While his most famous work is Moby Dick, it was surprising to learn that it was initially a failure. Impoverished, he ended his working life as a Custom’s Inspector at Castle Clinton. Moby Dick was later re-considered as a new genre of literature and attained great renown.

Hancock Shaker Village

The Shakers, adherents of a Protestant sect, came to the United States in 1774 with some members settling in the region around Pittsfield. They practiced communal living where property was shared, a separation of the genders, and no procreation. Initiation into the religion was by adopting orphaned children and by converting adults. Pacifists who practiced gender and racial equality, they numbered 5,000 at their height, and currently number two remaining followers who reside in Maine.

Started in 1960, this restoration, a short ride away from downtown, brims with furniture, household objects, art, textiles, commercial graphics, and an archival trove of 10,000 images that document Shaker life. 20 buildings on 750 acres feature over 22,000 Shaker artifacts. The Hancock Shaker Village offers a view into the life of this group and tells the story on the oldest working farm in the nation. A 200-year heritage of farming has culminated in an on-site working farm that practices historic Shaker farming principles and modern regenerative agriculture.

On site, the large 1830 Brick Dwelling slept 100 men and women in divided quarters with innovative Shaker design elements such as dumbwaiters and interior windows for sunlight and fresh air. Here you can view dormitory-style bedrooms, dining rooms, a kitchen, food storage rooms, and a meeting room, documenting Shaker life in the mid-19th century.

The ingenious Round Stone Barn, the only Shaker example, and an architectural icon, originally stabled 52 milk cows, and had entrances on three levels. Interpretive guides explain all about this structure and its unique design and practices.

Herb and heirloom vegetable gardens and a one-mile long loop trail are also part of the mix here, as well as a Museum Store that sells books, replica Shaker crafts, foods and seeds which make for a fitting end to a visit to this repository of the life of an almost vanished group.


Who are we when pushed outside of our comfort zone? Mindy Miraglia, Berkshire Camino Founder and CEO knows.

The 2010s were a tumultuous decade for her, starting with her return to the Berkshires in 2011, and working where she had grown up. Six years later, she found herself without a job, which gave her pause as to what to do next. She made the decision to tackle personal limits, and with the encouragement of friends and family walked the 500-mile Camino de Santiago across Northern Spain, twice in 2018 and 2019. With those trips came time for reflection. Meeting people along the way gave her the idea to give others, visiting her native Berkshire Mountains, a chance to push the envelope and observe nature’s beauty and reflect on their lives as well.

With a start in 2020, the curated tours are designed for guests who want to be challenged. One of their offered tours, perfect for a Berkshire Flyer getaway, is a four-hour, 5.7 mile walk, climbing 1,000 feet. This features an incredible vista of New York, Connecticut and Massachusetts sites then with a stop at the 2,150-foot-high Berry Pond, the highest body of water in Massachusetts, The descent is kind to knees and hips. Other longer tours are offered if you are so inclined, or shorter private tours by

prior arrangement. Mindy Miraglia knows, and has imbued her staff with the proper way to take over 55-year-olds and display nature in many ways we don’t even think about.


Barrington Stage Company, founded in 1995, enjoys national recognition, and has produced several award-winning plays and musicals. It hosted the world premiere of “The 25th Annual Putnam County Spelling Bee,” which was performed for almost three years Off- and On-Broadway.

After the industry-wide shutdown due to the coronavirus pandemic, BSC was the first Equity theater in the US to return to live performances. With the purchase of a former vaudeville stage in downtown Pittsfield in 2005, a former VFW hall in 2012, plus two other buildings, BSC is a formidable force in the regional theater world.

Since 1995, Barrington Stage produced 41 new works, 21 of which have moved on to New York and major regional theaters around the country, with the belief that new work is the heart and soul of theater. The current season has a full schedule until October, and a live performance is the perfect event to top off a Pittsfield Saturday night. Perhaps you will be ahead of the curve when you see that your BSC show will be coming to Broadway.


Located in the center of Pittsfield, the 120-year old museum has eclectic holdings that range from a 143-pound meteorite and exhibits of the Berkshire ecosystems, to a collected trove of paintings. Until October 1, “Romance and Nature: Art of the Hudson River School,” will be exhibited here, highlighting the museum’s Hudson River School collection, with works of Thomas Cole, Frederic Edwin Church, Edward Moran and others. With two floors of exhibits, and so many presentations to enjoy, it’s the prefect place to spend a few hours.

Downtown Lodging?

Downtown Pittsfield has two hotel choices for you in walking distance from the train station.


The 175-room Holiday Inn & Suites Pittsfield is located just a few minutes south of the train station. An indoor pool, a full-service restaurant, fitness center and a seasonal terrace, which offers expansive views of the Berkshires, enhance the 14-floor building. It’s within walking distance to most Downtown restaurants and venues.


The 45-room Hotel on North is a repurposed boutique hotel, which draws equally on heritage and innovation. It comprises two former mercantile buildings with thick walls and embodies the old and the new. Relaxed and casual, no two rooms are exactly alike, but each brims with modernity in its appointments. Beautiful furnishings, comfortable bedding, coffee-makers, well-lit bathrooms...the list goes on. The Berkshire Palate on the lobby floor offers a weekend brunch, lunch and dinner with a modern American menu. With a very friendly, accommodating staff, it’s location and proximity to downtown works well.

Food? Drink?

As part of a large agricultural belt in Western Massachusetts, Pittsfield has wide access to farm-fresh foods of all kinds; the food spots here take advantage of what’s locally available.

Walking distance from the hotels

District Kitchen & Bar - Close your eyes, listen to the chatter, and you would think you are dining in Manhattan. With a full beverage list and a menu that leaves little to be desired, this seems to be an outpost for creatives. The front is two storefronts wide, with large windows, infusing the restaurant with natural light; an absolute must for dinner or adult beverages. Closed on Mondays.

Dottie’s Coffee Lounge - A local favorite, and rightly so, this coffee shop is three storefronts worth of great coffee, fresh baked goods, and a Manhattan vibe. Open on weekends from 8am to 2pm, you may have to wait a little while to have your order taken, but it’s worth it. Owner Jess Rufo takes inordinate pride in what she does, and it shows. This is a shining beacon on North Street.

Hot Plate Brewing Company - Starting at noon, every day and into the evening, owner Sarah, and general manager and Brooklyn-native Mike, offer an even dozen brews at this sun-dappled side street location. If you cannot decide which beer to try, a flight is the ultimate solution. This a great place to rest from all the walking you will be doing.

King Kone - At 133 Fenn St., Pittsfield (Tel: 413/496-9485; no website) is a pleasant throwback to the 1950s — a basic, simple, ice cream stand offering generous portions and toppings. When Pittsfield native, actress Elizabeth Banks comes back to visit, she makes a beeline for this place. Nondescript this downtown location proffers ice cream daily 11am to 9pm. It’s worth visiting for the nostalgia alone.

Marketplace Cafe - A great place to pick up a picnic lunch or sit at tables outdoors for well-prepared fresh food, home-made lemonade and desserts. This is one of North Street’s best food assets. It is open for breakfast and lunch from 10am to 6pm except Sunday.

Methuselah Bar and Lounge - The vibe here approximates a busier East Side bar, with an eclectic menu that includes tacos and Korean food. Right on North Street, it’s close to the Barrington Stage. There are mostly stools and higher tables for seating. The kitchen serves from 5pm to 10pm, the bar from 5 to midnight. Check for availability of live music. Closed on Sunday

Patrick’s Pub - From 11:30am to 9pm except Sundays, this Irish pub, conveniently located around the corner from the Berkshire Museum, overlooks Park Square in the center of Pittsfield. Sit in or out, and the food and staff will win you over with an excellent meal from Buffalo Wings to a salmon platter.

Trattoria Rustica - Delving in Southern Italian fare, with many dishes cooked in a brick, wood-fired oven, in an interior of brick and stone, this Trattoria offers the best of Italy and Massachusetts. A small patio in back provides the proper outdoor atmosphere for an incredible meal. Open 5 to 9pm, Thursdays to Mondays.

A cab ride away, but worth it for the breakfast buzz...

Misty Moonlight Diner - Offering large breakfasts and lunches from 6:30am to 2pm except Tuesdays and Wednesdays, a weekend breakfast here is epic. From a breakfast sandwich to a Sirloin Steak Benedict, perhaps a moonlight burger with cheese, bacon, onion/peppers and an over easy egg, this is a place for all tastes. Look for all the Harley-Davidson memorabilia placed throughout.


Currently, Pittsfield has no active Mall, but some interesting shops have sprung up in the center of town. One place might have that tchotchke you must have...

Dory & Ginger- This home goods store is attached to Hotel on North with a variety of local candles, soaps, mugs, coffee table books and other Berkshire items. Open from Wednesdays to Saturdays, there will be something to bring back that will look wonderful in your living space as a memory of your Pittsfield trip.

Notes: Should you wish to go further afield, Pittsfield is central to the Berkshire Region of Western Massachusetts. For a longer stay, the Berkshire Flyer, which ordinarily travels to Pittsfield from NYC every Friday and returns on Sundays at 3pm. During the does 2023 three-day Holiday weekends, when it returns on Mondays at the same time, to NYC. Reservations should be booked as soon as possible as seats do go fast.

Casual, comfortable clothes and shoes will work well, perhaps some rain gear and a jacket for later in the summer. Hiking shoes for going up and down the hills might be a good idea.

For further information about what to see and do further afield in the Berkshires, see

Most of all, enjoy your weekend there!

Why not Guilford? Historic Town on Long Island Sound in Eastern CT

Sometimes the easiest decisions are also the hardest.

Upon arrival at the Guilford train station, there’s a dilemma—do you head towards Long Island Sound? Or do you stroll into “town”? Do you like old, small and local names on storefronts in a green central shopping area, learning about history a la Guilford? Better you should walk by Long Island Sound with a good meal or two, taking in some sea air as absolutely strangers say hello to you? Maybe a swim?

With over 380 years of a being a viable community (ironically 6 other towns in Connecticut are even older) a great place to start is the Henry Whitfield State Museum, a few minutes walk north from the rail station. Run by the State of Connecticut, the actual house, built in 1639, visitors center and gift shop are all open from May through October. Within the six months, about 4,000 visitors a year tour this historic space. Within the three story house are exhibits, furnishings, and artifacts from around the Guilford area. An on-site guide is there to explain about the houses origins and what has happened to it in almost 400 years. It is the oldest house in Connecticut and one of the oldest stone houses in New England.

Henry Whitfield, a Puritan minister who came from England to flee religious persecution, had the house built for his family; it was built as a fort to protect the residents of what later became Guilford during the 1600s. It was remodeled as a residence in 1868, then opened as a public museum by the State in 1899. Two renovations since then have tried to design what the house looked like originally.

Given its longevity as a residence, it has had its brush with boldfaced names; both George Washington and the Marquis de Lafayette separately visited twice, and Abraham Baldwin, one the signers of the Constitution, was born here. It’s web site address:

Should you visit on a weekend, the close-by 1713 Hyland House can be toured as well. It’s a classic New England salt box, with the 1764 Griswold House close to there; they are both open June-September during weekend afternoons. ( and


If you are walking from the train station, it’s a pleasant 15 minute walk down tree-lined streets to the bottom of the Town Green.

The Guilford Green is a flat, grassy rectangle with 125 trees planted throughout. The focus of the Green is a pink granite 1877 Civil War memorial, located near the center, with the Union soldier facing south. Those who perished during the war are carved on each of the four sides of the base. Other war memorials are scattered throughout the edges of the green. While the space now is a calm place to walk and think, at one point, it was the focal center of all town-related activities between the 17th and 19th centuries–a mélange of buildings, headstones, churches, and schools. The green at one time boasted a blacksmith, cattle, and up to 1,600 graves. In 1800, an academic stopped here on his way to write about Guilford as part of his communities research. Appalled by the lack of organized use, his unkind words convinced residents to mend their ways. Interestingly, while the headstones were moved to proper burial grounds, those interred beneath the Green have not been moved.

The Guilford Preservation Alliance offers a Town Green Tour by appointment. On it, 375 years of history come alive under the aegis of guides, as you stroll the periphery of the green. Houses and local buildings and there histories are discussed, along with Native American history, slavery, a Guilford native’s participation in the Salem Witch Trials, and even the Statue of Liberty; all play a part in the town’s history. The tour that leaves from the information center just north of the Green, lasts over an hour on flat streets. At this time, there is no descriptive website. For information, email or call 203-671-9351 to set up a tour.

The Marketplace at Guilford Food Center - if you need a quick lunch or late breakfast before or after touring, this is the place. An extensive menu of freshly-prepared sandwiches, salads and baked goods will amp you up for peripatetic wanderings. It’s at the heart of the Town Green—they do close in the midafternoon.(


Depending on your preference, you could head south the moment you arrive in Guilford, or head here for a final activity or two.

About a fifteen minute walk lies Jacobs Beach Park, which lies on Long Island Sound. If you are used to Jones Beach or a Rockaway Beach, this is different. This is a local town beach, somewhat compact with limited facilities (there is a fresh lemonade stand), but it’s size and the tiny waves make for an intimate outing. Unlike the beaches that are familiar, Guilford has an in-season, non-residents pass fee. For over 55s, it’s $35.00 per person, but you can visit as many times as you like. (

Should you want to start your visit with lunch, or wrap up, your trip with a seafood meal before the journey back to NYC, there are a few candidates within 10-15 minutes of the station, and close to each other to see which one calls to you more.

The Guilford Lobster Pound–open from Mid-May until, Columbus Day, this small restaurant offers fresh lobster rolls, lobsters and hot dogs on an enclosed deck with some marina and Long Island Sound views, from the marshes to open waters. They offer a clear clam chowder that strongly needs consideration in your order. Evening closings vary by the day of the week (

Guilford Mooring–This restaurant is next to the Pound, and offers a full menu indoors and outdoors. With an emphasis on fish, there should be something on the menu for everyone. There is a bar here, offering a wide selection as well. Certainly a great place for a celebratory meal after a day’s outing in a unique Connecticut shore community. (

Pa’s Place–unlike the other two, this small stone house with a porch also on the waterfront, offers breakfast, lunch and dinner in a cafe, casual, relaxed, and yes, during the season, there is outdoor seating. Three kinds of avocado toast, fried chicken, a scallop roll...the list is almost endless. from early, or until 7PM during the week, 4 on Sundays. (


Connecticut Shore Line East connecting trains arrive from New Haven (an east connection with Metro North or Amtrak) at 10:43 a.m. or 12:42 p.m. during the week and 11:16 a.m. or 1:17 p.m. on the weekends. There are earlier and later trains, but these time work best with museum and dining early closures. Also, this is a vacation, of sorts. Do you really want to make a train earlier than 8 am from NYC?(

If you do rent a car or drive your own, I-95 traffic can be fierce on weekends, and weekday rush hours. Once you are near the Town Green, or the historic sites, parking isn’t too much of a problem.

Make sure you look at their websites carefully to note the day and time closures as well.

It won’t hurt to carry some water with you, as well as sunscreen. There aren’t any tall buildings here, and shade could be at a minimum on your walks.

From the Sound restaurants, past the rail station, to the green is about a mile and a half—if you don’t want to hoof it, Lyfts and Ubers are available and the waits shouldn’t be too bad.

Above all, enjoy your trip!