Fall Escapes : The Berkshires , Massachusetts
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apple picking , cider doughnuts , hiking trails and an onsite winery and cidery . We sample the JMASH cider collection and leave with a bottle of Furnace Brook Winery chardonnay .
SUNDAY EVENING : We check into our second night ’ s accommodation , the Lakehouse Inn ( lakehouseinnlee . com ) in Lee . Purchased by Inderbitzen and Pillai last year , the Lakehouse offers the same amenities as the Cornell at a serene waterfront property with a clean white interior and wraparound porch . We drop our bags and grab a quick dinner of grilled chicken and steak Terranova at Barrington Brewery and Restaurant ( barrington brewery . net ) in Great Barrington . I take a four-pack of the Barrington Brown to go and note the après-ski-style bar would be perfect on a chilly fall night .
A storm breaks as we head back toward Lenox , threatening our outdoor performance at the award-winning Shakespeare & Company ( shakespeare . org ). The setting sun emerges just in time to create a stunning backdrop to the Roman Garden Theatre , one of several venues the company maintains on a former boarding school campus just outside of town . After the show , we spend a few minutes back at the inn enjoying the sounds of the lake before turning in for the night .
MONDAY MORNING : A lazy morning gives us plenty of time to explore the property , including the kayaks down on the lake . Beginning this past July , the Lakehouse is home to Oasis Bar and Grill ( lakehouseinnlee . com / oasis-bar-grill ), an outdoor dining experience featuring live local musicians on a clifftop patio overlooking Laurel Lake . The restaurant isn ’ t open during our stay , but we preview the patio during a leisurely outdoor breakfast . This time , I indulge with abandon , nibbling at the warm pastry basket and digging into fluffy French toast served with bacon , fruit and five-spiced potatoes . We reluctantly pull ourselves away from the view and pack up our things before heading south out of town .
MONDAY AFTERNOON : Passing through Great Barrington , we grab lunch at the Great Barrington Bagel Company and Deli ( gb bagel . com ), a classic New York-style bagel joint featuring matzo ball soup and all the spreads you could possibly want . A half-hour drive south , Bash Bish Falls State Park ( mass . gov / locations / bash-bish-falls-state-park ) beckons with its pristine views and thundering waterfall . We skip the steep hike from the Massachusetts side and instead park on the New York side of the falls , where a gentle incline climbs beside a brook . Though access to the falls themselves has been closed since 2022 , you can still enjoy the view from an overlook . Save some Instagram shots for the ride home , when the Berkshires scenery unfolds in miles of pastoral bliss all the way back to I-90 .
Fall Escapes : Chatham , Massachusetts
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full of excited families and nature enthusiasts . The tour guides regale us with waterfront tours of local Chatham institutions and neighborhoods on our way out to Monomoy , where , of course , the highlight is finally coming across the many curious ( and adorable ) bobbing seal heads poking above the surface .
FRIDAY AFTERNOON : Lucky for our rumbling stomachs , lunch options are already waiting for us right by the docks when we return . Though Dockside Cafe ( docksidecafeharwich port . com ) has regular restaurant service , we opt for its quicker walk-up window and get our fill of chouriço and clam chowder and fried codfish tacos .
Our initial plans included exploring the Monomoy National Wildlife Refuge ( fws . gov / refuge / monomoy ), known for its eight miles of protected sand , dune and marsh habitats , but the rain won ’ t let up ( there ’ s always next time !). Instead , we return to Main Street for a bit of retail therapy . The shopping is reminiscent of Thames Street in Newport , where clothing boutiques , specialty shops and even the odd national brand like FatFace dapple the way . My personal favorites include Ducks in the Window ( Love Batman ? Ruth Bader Ginsburg ? Construction ? They ’ ve got a rubber ducky for that .), Jaks Chatham ( I found my new favorite crewneck among its shelves ) and the Squire Shop ( more on that later ). ( ducksinthe window . com , dflax . com / chatham _ c _ 30 . html , chathamsquireshop . com ).
FRIDAY EVENING : We stop back at the inn to change ( read : forgo our sea-sprayed attire ), then head back out for a cheap and casual bite from Mom and Pops Burgers ( momand popschatham . com ). I am caught between the
El Dyablo cheeseburger and the buttermilk fried chicken sandwich at first , but the jalapeno-topped beef won out ( or lost , depending on how you look at it ) in the end .
It wouldn ’ t be a true Cape getaway without an ice cream stop . While there are plenty from which to choose , we are most intrigued by Short ’ n ’ Sweet ( facebook . com / shortnsweet chatham ), a big yellow house-like building we passed earlier in the day . Delightfully old school with cash-only registers and chalkboard menus , employees let us sample a few flavors like the coffee Kahlua brownie , but my friend and I ultimately settle on Oreo and black raspberry , respectfully . We enjoy our sweet selections in the attached seating area surrounded by quirky memorabilia and throwback tunes from the jukebox .
There ’ s just one more stop to make . While shopping on Main earlier , we had stumbled upon the Squire Shop , a supplemental gift shop to the Chatham Squire ( thesquire . com ) across the street . Its license plate-themed merch has us intrigued , to say the least . Though the Squire has an expansive dining room , we quickly realize the tavern is clearly the place to be on a Friday night . We miraculously snag seats at the bar and take in the walls studded with license plates from all over the East Coast and beyond ( though , suspiciously , I cannot find a single Rhode Island plate ). The beer selection is worth writing home about ( it redeems itself by having Narragansett on draft ) and the rotating lineup on the calendar of events , like karaoke and trivia , entices us enough to return sometime during the week . We mingle with fellow tourists and friendly locals alike until it ’ s time to call it a night .
SATURDAY MORNING : Time to get back to reality , but not before hitting one last place on Main . After checking out around 10 a . m ., Chatham Cookware ( chathamcookware . com ) is waiting and ready with nitro cold brews and hearty egg and cheese options sandwiched between Portuguese muffins to fuel our drive back . We may also make a detour to Devil ’ s Purse Brewing Company ( devils purse . com ) for a pint . When it rains , you might as well let it pour , right ?
Fall Escapes : Portsmouth , New Hampshire
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died orange peel . Treasures in hand , we travel to Portsmouth
Book and Bar ( bookandbar . com ), an ingenious
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