Why You and Your Pals Must Plan a Trip to Georgetown This Fall

We all know the Smithsonian museums are great, as is the National Mall, and a White House tour (bonus points if you were a cute kid and shook the President’s hand). But amidst all this culture and political clout, you may be overlooking one delightful D.C. district: Georgetown.

It’s brimming with history (it was actually founded before D.C. in 1848 and is currently a National Historic Landmark), gorgeous homes, stellar eateries, shopping aplenty, and, yes, those famous cupcakes you’ve heard all about. There’s also plenty of outdoor action at Georgetown Park along the Potomac River and the C&O Canal cuts right through the winsome quarter. Ahead, how to make the most of a group getaway to Georgetown.
 

As any traveler knows, where you make your home base sets the tone and itinerary for your entire trip. Kick things off on the right note at Rosewood Washington, D.C., where things are anything but cookie cutter. Walking in, you feel more like you’re at an intimate neighborhood building than a hotel, and the lobby has the most welcoming of sitting areas complete with a library, comfy seating, and a cappuccino machine.

Or, to the right of the lobby, you can walk right into CUT Bar and Louge by Wolfgang Puck and grab a drink or bite at the bar. Check into your very own townhouse — starting at $1,500 per night, they’re certainly a splurge but up to four guests can split the elegant space (use Zelle® to make splitting your reservation costs a cinch.) The hotel also has a charming rooftop lounge, CUT Above, with sweeping views of the city, a rooftop pool, bespoke bikes and picnic catering on offer, and CUT, the upmarket bistro from WP where the Maryland Blue Crab fried rice is something you’ll want to order again and again. Ditto for the brioche French toast and buttermilk-buckwheat pancakes you’ll be gobbling up here for breakfast, chased with stellar coffee.

For something more affordable, post up at Pendry Washington DC - The Wharf (from $645 per night), in the newly developed waterfront harbor. It’s about a 20-minute car ride to Georgetown and the spa and outdoor pool here are pretty epic.

Centrally located to both the waterfront and the historic homes district, Rosewood Washington, D.C. is just a few minutes walk to the meeting point for D.C. by Foot’s fabulous historic Georgetown walking tour, right along the C&O Canal (in Chesapeake And Ohio Canal Historical Park if we’re being technical). We don’t want to give too much away, but on the tour, you’ll see handsome homes in Federal-style architecture, the former haunt of JFK and Jackie O., and Martin’s Tavern, a beloved local pub established in 1933 that’s said to be where the Kennedys got engaged. You may also learn about one very suspicious escape act from a Russian spy at a French restaurant. The tour concludes by the bucolic Georgetown University campus, which you’re free to explore at your leisure — ask the friendly guides to point you in the right direction or give you a restaurant recommendation or two. If the spooky side of things is more your scene, you may also want to consider the outfitter’s ghosts of Georgetown tour. Low on cash? Ask your tour guide if they accept Zelle® as a fast and fuss-free way to provide them with gratuity.
 

Okay, we know it's mentioned above, but we’d be remiss if we didn’t share a bit more about this Georgetown institution. Celebrating its 90th anniversary this fall, the cozy venue (think: wooden booths, Tiffany-style lamps, a bartender that knows regulars’ names) has hosted every U.S. president from Harry S. Truman to George W. Bush to President Biden, as well as political bigwigs, foreign dignitaries, celebrities, athletes, and musicians. Request to be seated in the "proposal booth" if you want to ladle up your French onion soup and petite crab cakes in the same spot as the Kennedys.

Other local spots in Georgetown to add to your list: Brasserie Liberté for French fare and Farmers Fishers Bakers to chase your brunch and Bloody Mary with Potomac River views.

Georgetown’s waterfront, the Washington Harbour is a mixed-use development with running and biking trails, restaurants, a grand fountain (that turns into an ice skating area in the winter), and boating access to the Potomac River. In the spring, summer, and fall, we recommend booking an outing with SeaSuite Cruises for a retro boat rental or boozy, tiki boat adventure. Or, hop on the Potomac Water Taxi operated by CityCruises, connecting Georgetown to Old Town Alexandria, National Harbor, and The Wharf.

Whether you seek art galleries, home design stores, or clothing and jewelry, Georgetown delivers. M Street is the main drag with tons of retail outlets and mainstream names (Away luggage and Italian furniture group B&B Italia are two newcomers), but we suggest venturing off to quieter streets. Meander over to nearby Cady’s Alley, with restored row houses hosting high-end stores and showrooms parallel to the C&O canal. If you’re a home decor enthusiast, you’ll also want to swing by Manse, a housewares' emporium with no shortage of artisan goodies that opened in October, and furniture designer Molteni&C once it’s slated to open this winter.

Georgetown and cupcakes go hand in hand. And if you and your friends would like to go hand-into-mouth with such a treat, you’ve come to the right place. Baked and Wired is a must for its red velvet cupcakes, vegan Oreo cupcake, and a slice (or eight) of the swoon-worthy banana bread. Avoid lines by ordering ahead online for same-day pickup for you and your pals and have them reimburse you for their orders via Zelle®. Georgetown Cupcake also allows pre-orders but requires notice the day before; from these famous cupcake slingers, we’d steer you towards the double milk chocolate birthday cupcake, chocolate ganache, and the vanilla and chocolate. If you’re craving something savory as a lead-up to your confections, book it to Call Your Mother, a Jewish deli, where you’ll also want to order online to skip the lines.

One of the nicest parts of traveling is exploring a new city by foot, stumbling upon postcard-worthy scenes and unexpected restaurants that wind up being your favorite memories from a trip.

Georgetown is perhaps one of the most attractive walkable neighborhoods in the U.S. with its cobblestone sidewalks, gas lanterns, brick row houses, and the C&O Canal snaking through it all. Yes, it’s a bit hilly and some of the streets could use some paving, but wandering around this district is really a delightful way to spend a morning or afternoon marveling at architecture and popping into stores and cafés. Part of the magic is stumbling upon your own gems, but some steps in the right direction include any that take you towards the gardens of Tudor Place and Dumbarton Oaks Gardens, catching a live jazz show at Blues Alley, and noshing at Kafe Leopold, Fiola Mare and Chez Billy Sud.

Our personal favorite amble is from the C&O Canal along the Washington Harbour to The Watergate Hotel (if you start around the Rosewood Washington D.C., it’s under 15 minutes total). Before a veritable feast at the storied hotel’s Kingbird (which should definitely include the tagliolini with Maryland blue crab, red pepper tomato sauce, bottarga, and bread crumbs), ask kindly at the front desk if the Scandal Room is occupied. If not, a staffer should be able to take you up to the infamous room, originally room 214, that was HQ for the 1972 Watergate break-in. It’s outfitted with authentic artifacts from the era like a typewriter and tape recorder, book collection, and framed periodical covers and articles.

Biking is another solid option in these parts, and easy to do with bike rentals from Rosewood Washington D.C. or via Capital Bikeshare, where you can rent a bike from one docking station and return at any of the hundreds around town for $8 a day. There’s a pretty toe path from Washington Harbor, under the Kennedy Center, to the Lincoln Memorial. The flat, one-mile path follows the Potomac River and is great for a jog, too.

Worth noting: There’s unfortunately and infamously no Metro (the underground) stop in Georgetown. To get around via public transit, you can use the DC Circulator, red buses that run in 10-minute intervals. From Georgetown, the yellow line runs through the heart of downtown to Union Station. The blue line connects Dupont Circle and Rosslyn via Georgetown. Fare is a dollar and you can pay with cash or use your Smartrip card or app.