Want to get a bunch of shopping done without endless driving around and hunting parking spaces? You owe yourself a visit to Montgomery Row in Rhinebeck, where a curated selection of neighboring shops offers essential goodness—books, toys, fine clothing, hand-dipped chocolate, gourmet olive oil, home goods, skateboarding gear, baby and children’s shoes and clothing, fine paper, and unusual pet goodies. After treasure hunting, you can grab a great cup of coffee or a fine meal, get your hair done, wander an art gallery, and treat yourself to a boutique, small-group fitness session. It’s the perfect blend of coziness, convenience, and cachet—Bill and Hillary lunched at Gigi Trattoria here when Chelsea’s wedding brought them to town—without a whiff of snobbery; in other words, Montgomery Row is quintessential Rhinebeck.
Piper Woods grew up in Rhinebeck, where her family owned a car dealership and repair shop. She went on to study environmental science and geography at Ohio Wesleyan University. “I had a vision for this,” she says of the property’s transformation 22 years ago. “I’m passionate about small business; I feel very strongly about community and collaboration, and I wanted to make a destination that would serve everyone involved. It’s really more of a lifestyle center than a shopping mall—but part of the ethos is that you can find wonderful things here in any price range.” When Montgomery Row added a second building in 2004, Woods’ environmental science background led her to go with a geothermal system long before most developers had it on their radar.
At Montgomery Row in Rhinebeck, a curated selection of neighboring shops offers essential goodness.
Some of the shops in Montgomery Row, such as Oblong Books, Changes (men’s clothing) and Hammertown, have more than one location, but all 21 are expressly chosen for consciousness, ethics, quality, and variety. “One of the things I’m super passionate about is finding businesses that have a really great concept and a unique point of view,” she says. “And we’ve been super lucky to build the community that we have here. Everyone is so smart and dedicated to welcoming customers. We pack a great, unique experience into this block-and-a-half.”
All six of the first tenants—Gigi Trattoria, Changes, Hammertown, Oblong Books, Paper Trail, and Xanadu Hair Studio—have stayed and flourished, building Montgomery Row’s reputation as a destination that Hudson Valley magazine readers have voted “Best Shopping Block.” “I both like and love all my tenants,” says Woods. “I’m super blessed to have them, and I do all I can to support their success. If they’re successful, I’m successful.”
Suzanna Hermans is co-owner of Oblong Books, named after the unique strip of land 20 miles off the Hudson that was claimed by both Connecticut and New York in the Colonial era; Oblong’s other outpost is on the Connecticut border in Millerton. “We’ve seen an amazing resurgence of independent bookstores in the past decade,” she says. “The chains decimated the landscape in the ‘90s, just as malls and shopping centers did to small retail generally.
“I’m passionate about small business; I feel very strongly about community and collaboration, and I wanted to make a destination that would serve everyone involved.” – Piper Woods, owner, Montgomery Row
But people have moved on from that a bit; we’ve realized we really want vibrant landscapes full of interesting small businesses in our communities. And the business model of a huge chain bookstore just really never made sense; it takes an awful lot of money to fill and staff a space that big, and people didn’t really bond with those places. I don’t need to physically have a book in my space to get you access to it; we can get you any book in the world in just a few days. So we focus on making it magical.”
“Those of us in the original building, we’ve all been there for 20 years, which makes for a really cool work life. I think that’s a huge testament to Piper, her vision for this space, and her commitment to her tenants.” – Suzanna Hermans, co-owner of Oblong Books
Hermans’ father founded Oblong’s Millerton store in 1975. “He lives in Pine Plains, so that location made sense,” she says. “Piper reached out to him back in 2001, when she was converting the property, and Dad was smart enough to see it as a great opportunity to expand at the right time.
I was in high school then, not paying a whole lot of attention, but I’ll never forget our opening—it was September 15, 2001, four days after 9/11, and people needed to connect, to process. We had people coming in just to talk before we even opened, while we were setting up.
I still get goosebumps remembering them walking in with pale, exhausted, anxious faces. It was a somber time to open a store, but an important one—our bond with the Rhinebeck community really began right there.”
Hermans has transformed herself from a teen to the sort of indie book merchant who gets profiled by Kirkus and asked to judge literary contests; along the way, her appreciation for Woods’ management style has only grown. “Piper’s a dream landlord,” she says. “She’s committed to supporting her tenants at a level that, from what I understand, is extremely uncommon.
She organizes group advertising; she’s recently been helping us do billboards together and covering some of the cost, which is prohibitive for an individual small business. She gets it that you can’t just fill your space and walk away; you need to continue to support the businesses throughout their tenancy and then they’ll stick around. Those of us in the original building, we’ve all been there for 20 years, which makes for a really cool work life. I think that’s a huge testament to Piper, her vision for this space, and her commitment to her tenants.”
All of this, of course, translates into a retail experience as deep and broad as it gets. Alongside the shopping, dining, boutique fitness classes, and art, one can schedule financial consulting or a therapy session, get a haircut from folks who styled Clinton wedding guests, or arrange for website design or some market research. There’s a lot to shop for in this blended block.
And because they’re having fun, so will you. “We really do cater to everyone,” says Woods. “You can go into Hammertown or Paper Trail or Krause’s Chocolates, into Starrybird Kids or Oblong, into any of our stores really and find something that appeals to you or to whatever unique individual you might be shopping for, across all kinds of price points and across every demographic, something for every taste. I love the fact that loads of incredibly varied people take the opportunity to enjoy the destination we’ve created here.” For seasonal discounts and rewards, customers can sign up for Montgomery Row REWARDS at montgomeryrow.com/promotion/montgomery-row-rewards/ Their most popular promotion, SHOP, DINE, INDULGE, is in November & December.
6422-6423 Montgomery Street, Rhinebeck