Great Dates in Fifty States: Boston and Environs – Part One

800px-Charles_River_Esplanade_-_IMG_3777Hullo, Gentle Readers. Yes, it is I, your GGG. It occurred to me that, although I’m terribly romantic at my core, and although I’m a lifelong resident of Boston, I’ve never written a Great Dates in Fifty States article. This is shameful, and I have decided to rectify this at once!

You may not think of Boston as the most romantic city, but we are. Some call us the Hub of the universe, but I say we’re the Hub of Love. What could be more romantic than a city chock full of history, adventure, and awesome foodstuffs?

Now, admittedly, my idea of romance may not be yours, and anything I suggest will have at least a vaguely geeky slant, but I can guarantee you some unique and romantic encounters that are not your run of the mill dinner and a movie.

I Love That Dirty Water

So, let’s start with an overview Boston itself. It’s a wonderfully accessible city, not too big to walk around, but blessed with a great system of public transportation. The one way to get around that’s not enormously wonderful in Boston is by car or taxi. Yes, both are fine, but parking is absurdly expensive here, and taxis are as well. If you’re so inclined, think of taking advantage of day passes or pre-loaded Charlie cards for our public transport system, the MBTA (also just called the T.) If you prefer, you might consider the Hubway, a series of bike rent and return stations. That could be part of the date itself.

Boston is comprised of numerous neighborhoods—far more than I could cover in even a series of articles. There’s the downtown area around Boston Common & the Public Gardens. There’s Back Bay, encompassing well-known areas like Beacon Hill. There’s the South End, with the remnants of Boston’s gay “ghetto”. There’s the Theater District, Chinatown, Copley Square, Newbury Street, and a ton of other neighborhoods, each with its own character.

Parks & Picnics

The heart of Boston’s downtown area are a pair of linked parks—Boston Common and the Public Gardens. You could make a date out of simply walking around and exploring these gardens. The Common has a large public pool which becomes an ice rink in the winter. The Gardens have the swan boats, a fine way to enjoy a leisurely ride on a bit of water. Both have beautiful states, including a charming salute to the book Make Way for Ducklings. At the right times of year, you can find all kinds of free concerts, theatrical events, and festivals happening here. usually has the lowdown.

If you need a good place to pick up high end goodies for a picnic on the Commons, begin by hopping off the T at the Charles St./MGH station and stroll down Charles Street. You’ll find plenty of swanky places to grab a bite to eat, but you can make one of the most amazing picnics ever by making stops at three places. Savenor’s is a store that Julia Child used to visit all the time. Although they’re famous for their exotic meat section (you can buy everything from wild boar bacon to kangaroo, bear, and zebra), you can also purchase incredible pates, breads, cheeses, and desserts. If you trust your GGG, however, you’ll save your dessert dollars for a trip to Beacon Hill Chocolates, where you can find Sea Salt Caramels in Dark Chocolate, Candied Bacon Caramels, Caribbean Rhum Raisin Truffles, and Chile-Limon Mayan Truffles, and much, much more. Yes, they will be expensive; they will also be worth every penny. Then, just before you cross Beacon St. to the parks, you’ll stop at DeLuca’s, Boston’s oldest grocery store. Here, you’ll buy anything and everything else you might want for your picnic. Their original location is closed due to a fire, but their wine cellars are still open, and they have a selection of other treats as well.

For something a little different, make your walk down Charles St., but then make your way instead to the Charles River Esplanade. This long, rambling stretch of park next to the no-longer-quite-so-dirty-waters of the Charles River is a beautiful place to explore. You’ll find another public pool, boat landings, playgrounds, areas ideal of biking and inline skating, and the Hatch Shell, often host to events like concerts by the Boston Pops and free movies.

For something quite different, take your picnic to Boston’s waterfront district and hop on a ferry to the Boston harbor islands. Although there are several islands to choose from, my favorite is Georges Island, which is dominated by the Civil War era Fort Independence. Not only is this an awesome place to fly kites and play Frisbee, it’s also a great place to explore. You’ll find rambling buildings and chambers, and you can even keep an eye out for the Fort’s resident ghost, the Lady in Black.


If upscale picnic is not your idea of a good time, you’ll be just fine. In the opposite direction from the parks from Charles St. is the Theater District. This area has fantastic shows running pretty much constantly. Everything from Broadway hits to small venue plays will be going on, and, if you like great music and weird, quirky theater, you could do worse than heading to the Charles Playhouse to catch Boston’s version of Blue Man Group. If you’ve seen Blue Man Group in other cities, this won’t hold any surprises, but if you’ve never seen it, you’re doing yourself a disservice. Go see it.

A number of excellent little restaurants lurk all around the Theater District, ranging anywhere from food court experiences to a number run by celebrity chefs. My favorite actually fronts on Boston Common and is called Remington’s of Boston. It’s more of a pub than anything else, but they have one incredible feature. If you’re going to a show, you can tell them, and they will make sure your food gets to you in plenty of time to eat, enjoy, and then get to your show. I’ve never had a bad meal here, and my Dad and I used to go to a lot of plays together. (Really, my coming out shouldn’t have surprised anyone.)

For the ultimate dinner and a show experience, however, I recommend going a little outside of the box…and the city for that matter. Just south of the bustle of the downtown is an unassuming little building that hides one of Boston’s most amazing and longest running theatrical events (40 years as of 2013)—the Medieval Manor. Put all thoughts of Medieval Times out of your head. This is a small venue that serves excellent food, plentiful alcohol, and a raucous, bawdy, musical show. The jokes are groaners at times, but we always laugh at them anyways. If you don’t like to be dragged into interactive theater, then stay away, because there’s almost no way to avoid it. But if you’re a good sport and don’t necessarily mind the idea of having to ask the King’s permission to go to the bathroom (take the road to Canterbury), then go. Let’s face it…nothing inspires romance more than a few good-natured laughs at one or the other’s expense. Don’t hesitate. Just go. But make reservations! It’s a terrifically popular show.

Only Part One

Goodness, I feel like I’ve hardly scratched the surface of Boston, let alone the great towns around it, and this is already a long article. In follow-up articles, I’ll tell you about some of Boston’s awesome museums and some unique ways to see the sights, as well as a patriotic path to follow, and some cities outside of Boston that’re must-visits, too.

About GGG

Andy/GGG is a gay geek guy for sure. He's been playing D&D since he was 10, and he equates reading Tolkien with religion to some degree. He's a writer/developer for a Live Action RPG called The Isles, and he writes a comic called Circles, a gay, furry slice-of-life piece that comes out way too infrequently.

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