My incredible friend Alex (you may remember her as the founder of Persifor, one of my all-time favorite clothing companies) is here today with a guest post on two local family getaways. She is a pro at planning trips and scouting out the coolest activities, restaurants, and hotels. You can find more of her getaway recs as highlights on her Instagram.
I actually followed her tips and planned a little weekend getaway to Woodstock, NY a few months back and we had a blast! If you’re looking to book a family getaway this fall here are two great options fully planned out for you. Take it away, Alex!
Back in October, I started to unwind. I missed travel and “seeing” fresh design outside of Instagram, my only resource beyond the coffee table books and magazines that littered my living room floor during the days we were shut down in the house. I was apathetic, my creative ingenuity was burnt and I recognized the absolute need (yes, need) for a change of landscape to re-energize.
Since a sojourn to Sorrento was out of the question, I began to research “local” New England adventures while bearing in mind suitable COVID safety measures (and the statewide mandates at the time of travel). A few things that I considered when picking these destinations: A variety of outdoor activities and dining options; the ability to book timed indoor excursions (at museums and historical sites); and finally, comfortable and clean sleeping accommodations that also felt special and could use small-business support. Below are my itineraries through the Berkshires and the Catskills, with a few insider tips Apeppered throughout based on my personal experience and feedback.
The Berkshires: For the Art and Outdoors Enthusiasts
In early October (when Massachusetts wasn’t included on Connecticut’s list of restricted states), my husband and I spent 24 hours touring the Berkshires. We fit a lot into the time we finally had away from our kids, doing things that are typically more difficult with small ones in tow.
A major travel publication had recently published an article on the little–known destination of North Adams, Massachusetts at the northern tip of the Berkshires. I had never been through the towns dotting Route 7 so I planned our excursion from coastal Connecticut through Great Barrington and Lenox with a final stop in the artsy town just south of the Vermont border. The road trip was the perfect combination of great outdoor activities, farm-to-table meals (that I didn’t have to cook and clean), and seeing new and innovative art and design. For a map of dropped pins and additional recommendations, click here.
Visit: The Mount at Lenox
Home to one of America’s greatest female writers, The Mount is the brainchild of Edith Wharton, who is best known for literature greats like Ethan Frome, The Age of Innocence and The House of Mirth. While the historic house and it’s now trendy “grand-millennial” interior design vibes are typically at the epicenter of its fanfare, we chose to spend more time walking the grounds and experiencing the magnificent gardens during the transition from summer into fall. It should be noted that during the winter months, the interior of the home is closed but the grounds are still open to the public.
*Tip: You can enjoy coffee, pre-boxed lunches and sweets on the deck of the house overlooking “Lime Walk” and the linden trees that line the manicured paths.
Eat: Marjoram and Roux
At the top of Railroad Street in Great Barrington sits this little café hidden discreetly behind a wash of black paint and bright green plantings. Behind the subtle façade is a Scandinavian inspired interior and equally modern menu that utilizes local purveyor’s best ingredients; lettuces from Equinox Greens in Sheffield, pastries from the Break Room (you’ll read more on that later) and coffee from Barrington Coffee Roasting Co. We ordered the frittata du jour and paired it will the cauliflower bisque before diving into a chocolate croissant.
Just two doors down from Marjoram and Roux is indie apparel and home shop Griffin. The shop carries international clothing and accessory brands like Moismont, Malin and Goetz, and Save Khaki as well homewares and textiles sourced from South America to Southeast Asia. I was most inspired by their book section and the unique titles and subjects I hadn’t seen elsewhere.
Rubiner’s Cheesemonger: Put simply, this spot is the holy grail for anyone that enjoys artisanal cheeses, meats and European packaged goods (I couldn’t believe the extensive collection and variety of canned sardines). Outside the restored bank building are bushels of fresh produce from local farms, some vegetables I didn’t even recognize. Inside, the very best cheese, bread and wines curated from small batch producers. Don’t make the rookie mistake we did: Pack a cooler to bring back an assortment of goodies home, like the room temperature fresh French butter. Or if you’re unable to visit in person, they assemble and ship gift boxes nationwide.
Rest: Tourists Welcome
A riverside retreat inspired by the roadside motor lodge, Tourists Welcome is a 48-room single-story basecamp for design-driven naturalists. The perfectly cured blond wood finishes are synergetic with the hotel’s laid-back, feel-good energy but there’s also an intense level of focus on great service and attention to detail that can be experienced even on the website’s landing page. I chose this hotel for these reasons and because the owners took safety measures for its guests very seriously. At the time of booking (October 2020), the hotel required a three-night minimum (we paid for three but stayed for two because of childcare limitations) to enable the rooms to be fumigated and cleaned for a few days between guests. It’s pet and family-friendly, the Caravan rooms have lofted sleeping arrangements for 1-2 children and red wagons for carting around the property. The grounds also bolster access to the Appalachian Trail, outdoor wildflower and sculpture hikes, and a pool that is open during the summer months.
Tourists did temporarily shut down its main indoor dining area but set up Solo Stoves and outdoor tables for savory lunch and dinner snacks (spinach + artichoke dip and chicken pot pie were among the highlights) in addition to an amazing in-room breakfast service. I opted for the dairy-free strained yogurt, fresh fruit, and granola while my husband ordered the challah French toast with berries.
Tip: The Solo Stove seating needs to be reserved in advance so plan accordingly upon arrival and book your time at check-in.
Outdoor: The Ashuwillticook Rail Trail
A former railroad corridor converted into a 10 foot-wide-paved path great for walking, cycling (which is what we did), and even cross-country skiing in the winter months. The path is 12.7 miles long, each way but flat and do-able, even for novice riders. We packed our road bikes for the trip knowing that we would do this trail but there is a local shop in Pittsfield for rentals, Berkshire Bike and Board.
A revived cotton spinning mill and home to a culinary lab and craft cider distillery. After our ambitious bike ride, we landed here and went to the Greylock Works farm-to-table restaurant for a late lunch that included their fresh vegetable salad with pickled onions and green goddess dressing, vegetable wrap sandwich with roasted potatoes and hard cider from Berkshire Cider Project (made on-site). Oh, and did I mention the corn cookie? You can guess how that was…
See: Mass Moca
If I had to pick a museum facility for my first indoor endeavor during COVID, this would be the place. The industrial campus is vast, boasting 250,000 square feet of wide-open space. It’s this enormity of these galleries that enables the Mass Moca to showcase larger-than-life works that cannot fit in typical New York and Boston facilities. Permanent collections include the artwork of Sol Lewitt, Spencer Finch and Sarah Oppenheimer.
Tip: Include in your visit the immersive James Turrell’s Into the Light exhibit, it’s extraordinary and limited to three participants at a time. Like a lot of art, it’s tough to articulate the experience in words but it is worth delegating some time to this exhibit.
If you’re there during dining times, pay a visit to the taco truck parked in the center lot or park yourself at the picnic benches in front of A-OK Berkshire BBQ, best known for their brisket and southern comfort food.
Pit Stop: The Clark Art Institute
Headed out of town the next morning? Take a detour at the Clark Art Institute in Williamstown. Open through October 17th, 2021, the institute’s first outdoor exhibition features site-responsive works by contemporary artists Kelly Akashi, Nairy Baghramian and Analia Saban. We spent 45 minutes at the reflection pool in streamlined Adirondack chairs people watching and taking in the scenery. Advanced tickets are required. If you’ve had a little too much exposure to the arts, the Clark is also at the home to various Williamstown walks and trails, map included below.
Woodstock, New York: For the hippies (and their kids)
Let’s be honest, November and December were a bit of a rough run. School was still hybrid for many of us and the holidays just didn’t quite have the excitement of years past (a likely result of most scheduled “events” and visits to Santa canceled). My daughter and son had been staring at the same toys, the same tv screen and the same set of books for months. It was time to treat them for all of their hard work and durability to some time away from the house.
Cue my investigation into the legendary town of Woodstock, New York. It had been years since I had been to the Catskills (my last visit was to attend the second iteration of the music festival in 1999, which was cut short when concert-goers rioted and set the stage on fire) so it felt like a fresh destination that I was eager to explore with my family. For a map of dropped pins and additional recommendations, click here.
Stay: Hotel Dylan
I booked a reservation at “the Dylan” which came across my radar after asking a friend about Phoenicia a few towns over. Designed by the Novagratz’s, the two–story motel is brightly decorated with fun and whimsical finishes. It was also one of a few locations that had a set up for families with kids. The “Band Room” duplex where we stayed is two levels- a king sized bed and bathroom on the top level and a twin with trundle downstairs. I coordinated with Darryl the manager via text message about our contactless arrival and the room was ready by the time we pulled up to the front door. While the main lobby is closed to for the most part, you can borrow records and board games to play in your room from the front desk. The hotel also boasts outdoor fire pits on a first come, first serve basis and the ingredients for roasting s’mores are waiting for you in your room.
After our road trip, both kids were famished. I pre-booked all of our dining in advance of the trip (due to NY limitations on capacity), which was fairly easy given our typical 5:30 pm dining time. The staff was incredible- they ushered us to our socially distanced table quickly and let us know that they would be able to accommodate the kid’s “pickier” tastes with no problem. While my husband and I perused the menu (we ended up splitting the spinach ravioli with mushrooms and the truffle and rosemary goat cheese pizza), the waiter spirited over a breadbasket for kids. The restaurant is clearly sensitive to being expeditious in serving meals to families with small children which did not go unappreciated.
Eat: Phoenicia Diner
We rose with the roosters the next morning and piled the kids into the car for a 15-minute ride to the Phoenicia Diner. The restaurant has a cult following: Brooklynites and Stepford wives alike travel to the roadside establishment from NYC and beyond for comfort food cooking (their pancakes are legendary) sourced from Catskills and Hudson Valley farms. Currently, the diner is only offering outdoor seating under a heated awning but the nearby vintage Airstream and mountain views make for a great dining experience, even in colder temperatures.
Tip: The diner also has a sister spot in downtown Woodstock, Dixon Roadside, on Tinker Street.
Explore: Ashokan Reservoir Promenade
After a hearty breakfast, we ventured out to the 2.8-mile Ashokan Reservoir path. Flat and perfect for walking, jogging (or in our case, riding bikes and scooters), the location is perfect for getting a dose of fresh air and taking in the picturesque Catskill skies that are often punctuated with rainbows (we saw two the day we visited).
Shop: Tinker Street in Woodstock is best known for its local artist’s collectives and tie-dye, festival-themed shops. There is a great children’s toy store at the top of the circle as well as vintage clothing purveyor Three Turtle Doves and the quaint The Golden Notebook bookstore.
Tip: Hitting that mid-day slump? Visit Bread Alone for a signature triple chocolate chip cookie and espresso for the road- it’s just a few doors down from the aforementioned stores.
Play: Woodstock Elementary School Playground
Desperate times sometimes call for desperate measures. As much as my kids love to walk on trails, sometimes a school playground (and parking lot for scootering!) is just what one needs to pass the time and eliminate that rambunctious energy. It’s open to the public on the weekends and other families were sensitive to social distancing, wearing masks, and sanitizing hands throughout the times we were there.
The highlight of our trip was our final meal at Sylvia. An open kitchen with a wood fire grill, the restaurant creates unique dishes made from high quality, locally sourced ingredients– I ordered the Bibimbap with Korean beef barbeque, my husband the wood-smoked porkchop. The menu is elevated for most kid’s palettes- we fed our children before going and made sure to order some of the plainer appetizers on the menu for them to pick at during our meal. Their cocktail list is equally as impressive and includes a Pear Vanilla Hot Toddy and Blueberry Cardamom Smash Mezcal (which I tested and approve). I was most inspired by the modern but comfortable interior and exterior design of the space (outside dining was complete with picnic tables and fire pits for those that didn’t want to venture indoors) and the opulent floral displays positioned throughout the bar and table areas.
As borders open up and vaccinations roll out, more and more people are becoming comfortable with leaving their homes and embarking on their own adventures. Now is a great time to take advantage of some of the smaller crowds and access to hotels and restaurants that typically book months in advance. Added plus: Everyone that we met along the way was incredibly grateful for the support and patronage after a long and difficult year for the hospitality industry.