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Day Trip: Rhinebeck, N.Y.

Rhinebeck to the Future—chilling amid a village's retro indie charm

Editor’s note: The spring-summer issue of our print magazine “Out & About with The Berkshire Edge” is now available for free at 140+ high-traffic locations throughout the Berkshires and beyond.  Our magazine focuses entirely on places to go and things to do in the Berkshires during this three-month period. This article is a feature of that issue. Pick up a copy of the print magazine or read it online.

There was no clear escape plan. No idea when or how we’d extricate ourselves. The blinking lights, pulsating sounds, and poorly rendered graphics were simply too much to resist. The finality of “Game Over” warnings meant nothing to us. We had quarters. A lot of them. Lined up on the dash. Other players, the little redhead kid included, knew this was our machine. They gave us space.

Iron Maiden pinball at Megabrain Comics and Arcade. Photo Andrew Blechman

We made our rounds, slamming flippers and palming joysticks—outsmarting Blinky, Pinky, Inky, and Clyde amidst tasty pellets; swinging from vines to save Donkey Kong from Mario; and making as many bells light up as possible on the Iron Maiden pinball machine. 

“People should come here,” my teen daughter Lillie says, eyeing our last quarters. “This place is awesome. I’d tell people to come here.”

Despite its popularity, the village of Rhinebeck is not actually known for its back-of-store arcade at Megabrain, , Rhinebeck’s Black-owned comic book boutique that draws on a dedicated clientele. Rather, it’s typically associated with several hundred years of American history, spanning the Dutch settlement of the Hudson Valley through the Revolutionary War, to FDR’s fondness for the town and beyond. Today, Rhinebeck is a favorite of transplanted New Yorkers and visitors alike, who revel in its quaint-to-groovy indie stores, restaurants, and cultural offerings—and in the area’s natural beauty. 

The stately Beekman Arms, the nation’s oldest continually-run inn, pretty much sums up Rhinebeck’s historical relevance as a crossroads of American history. George Washington did indeed sleep there, as did Benedict Arnold and Alexander Hamilton (Aaron Burr—boo hiss!—mainly patronized a neighboring establishment that eventually burned down). It was here that Benjamin Harrison (not to be confused with his grandfather William Henry Harrison) and his running mate, Rhinebeck local Levi Morton, learned that they were nominated by the Republican national convention (they were elected but soon forgotten, their administration bookended by Grover Cleveland). And it was at the Beekman Arms that FDR concluded every campaign for governor and president by addressing supporters from the inn’s front porch.

FDR’s fondness for Rhinebeck likely evolved from proximity—his home in Hyde Park is a dozen miles downriver. As president, FDR took a special interest in the renovation of the village post office next door to the Beekman Arms. He insisted the building reflect the region’s historical Dutch architectural vernacular; hence the fieldstone walls and steeply sloping roof. Inside, the post office’s muralled walls are well worth a special visit. If you look closely, there’s even a nude male skinny dipper enjoying a refreshing dip with his mill coworkers. 

But it wasn’t the lure of history, despite a racy mural, that lured my teen from another game of Space Invaders. That honor goes to Aba’s Falafel down the street. Great Barrington residents may remember the always-crowded Aba’s Falafel stand at the local farmer’s market. The Israeli couple now have a lunch place that closes at 3:30 pm in downtown Rhinebeck. Nearly everything is made on premise, even the pickles and cilantro-garlic hot sauce (the pitas come from an Israeli baker in NYC). The restaurant is vegan and, apart from the pitas, gluten free. The falafels are simply irresistible: crispy on the outside, soft and crumbly on the inside. The sandwiches were more than enough . . . but that didn’t stop us from ordering a “seven for seven” (seven falafels for $7). Pushing pinball flippers is more of an aerobic workout than many give it credit for.

Streetside dining at Cinnamon’s. Photo Enjoy Rhinebeck

Other Rhinebeck food favorites include: Terrapin (located in a former church with a varied menu and family-friendly, comfy-bar dining); Cinnamon (authentic Indian with a Sri Lankan twist); Bia (modern Irish food; the name means food in Gaelic); Bread Alone (popular café with homemade baked goods and  sandwiches); Gigi’s Trattoria (for “local Hudson Valley Mediteranean”—order the Skizza!); Foster’s Coach House (local comfort-food mainstay with delightfully retro yet authentic décor); The Amsterdam (elevated farm-to-table); and Le Petit Bistro (upscale continental with a bistro flair). Smoky Rock BBQ, Aroi Thai, and Osaka (for sushi) are yet others. 

Rhinebeck’s proximity to the Culinary Institute of America may explain why the food offerings are particularly impressive. The Beekman Arms is a cozy place to dine as well. And, as times change, so does the Beekman: the revolutionary-era bar apparently has bragging rights to the best margherita in the Hudson Valley (not sure what George Washington would do with that tidbit of info). And if you’re there on a Sunday, don’t forget the Rhinebeck farmer’s market, one of the better ones in the region for dedicated foodies.

Morgan at Samuel’s Sweet Shop. Photo Andrew Blechman

Given that Lillie and I were a reporting duo, it might not come as a surprise that our next stop was the candy store—actually we made two stops there because apparently one visit isn’t enough. Samuel’s Sweet Shop is a Market Street mainstay, filled with retro candies (Twirl Pops, Pop Rocks, and Moon Pies) and homemade chocolate delights. The sweet shop comes with a bit of Hollywood glamour as well: it’s owned by Paul Rudd (Antman), Jeffrey Dean Morgan (Walking Dead), and Hilarie Burton (One Tree Hill). The three friends (Morgan and Burton are married) all have homes in Rhinebeck and stepped in to finance the store when it’s owner, Ira, died unexpectedly several years ago. 

Scoop your own potpourri at Periwinkles. Photo Andrew Blechman

East Market Street is full of hip independent retail stores. Lillie particularly enjoyed Periwinkles with its scoop-your-own potpourri, handmade soaps, and bath bombs; and the A.L. Stickle Variety Store across the street. Remember variety stores? Stickle’s sells gag gifts, cooking supplies, art supplies, moisturizers, lampshades, vintage toys, birdhouses, candles, local honey, and dolls, among other things. Proprietor Matthew Stickle tells us that when his grandfather Alfred Lee opened the store after World War II, he had more than 80 vendors. “He wanted to offer customers a little bit of everything,” Stickle says. “And back then a lot of companies made one item only, like Slinky or Playdough.” That was, of course, before the age of conglomerates. We enjoyed our taste of that simpler time browsing the curated chaos. Lillie walked out a very contented shopper with sidewalk chalk and bubbles. I bought myself a Neato Rail Twirler (a remake of the classic Whee-lo). Other browsing opportunities on East Market included the Land of Oz toy store and Winter Sun & Summer Moon, which has a stylish collection of clothing and global knickknacks. 

Two other strong indie presences in Rhinebeck are its top-notch bookshop, Oblong Books, and movie theater, Upstate Films. Like much of the village, both harken to a time when bookstore and theater proprietors personally curated unique and frequently outstanding offerings. I grew up in a town that had both, but these days such independent cultural businesses are rare enough to border on nostalgia. 

As with the Berkshires, the surrounding area is filled with biking and hiking trails. For biking, consider contacting Breakaway Cycles or the Rhinebeck Bicycle Shop. Two easy hikes with stunning vistas just minutes from downtown are yours for the taking: Drayton Grant Park at Burger Hill and Ferncliff Forest. 

If you’re familiar with Hurlburt Hill at Bartholomew’s Cobble, then Burger Hill will feel similar—a welcoming trail up an open grassy hill that culminates in a remarkable panorama of the Hudson Valley. Ferncliff has a similarly compelling vista of the Hudson River and Catskill Mountains with the added excitement of an 80-foot observation tower that’s just 15 years old. If you’re game for climbing up the 109 steps, you’ll be treated to an unparalleled view. Lillie bounded up; my acrophobia got the best of me halfway up. 

And if a quiet stroll with great birding and no vertical ascent is your thing, consider Vlei Marsh Preserve, for a very close-up view of the mighty Hudson nearby at Rhinecliff Landing, a waterfront park with a public boat launch.

On the hour drive back to Great Barrington, Lillie and I mull the things we’d like to return for. A hike up Burger Hill; an open-air biplane ride at the Old Rhinebeck Aerodrome; the Dutchess County Fair in August; maybe a trip to Hyde Park . . . “I’d definitely like to go back,” Lillie declares. “That falafel was amazing.”


Editor’s Note: Andrew’s daughter and travel companion Lillie assisted in the research and writing of this article. Their dog Gingerbread came along, too. 




The Edge Is Free To Read.

But Not To Produce.

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The Edge Is Free To Read.

But Not To Produce.