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This year Chol Hamoed falls with a Shabbos in the middle. While this might ruin your dream road tripping plans, it gives a unique opportunity to discover a new city in a laid back way and just enjoy strolling its streets. Below are a few options with beautiful walkable streets, an option for meals in the sukkah and lots to explore in the area.
Burlington, VT
Chol Hamoed Sukkos is the peak foliage season on the East Coast – which makes it the perfect time to visit Vermont. Unfortunately it also means limited availability and increased accommodation rates, but the views make it worth it.
Sukkah & Meals
Chabad of Burlington has a publicly accessible Sukkah at 80 Summit Street, Burlington, VT. They also host Shabbos meals which can be reserved on their site. Additionally, there’s an eruv! so if you’re staying in the area, you can come over with a snack at any time.
Stay
Since this is peak season, accommodation availability is quite limited. Below are some options that were still available when we checked.
- Chabad has a few guest rooms that can be rented. This is within the eruv and super convenient for sukkos.
- Hilton Garden Inn Burlington Downtown
- Hotel Champlain Burlington, Curio Collection by Hilton
- Double Tree by Hilton
- Homewood Suites by Hilton
- There were also a few options still available on airbnb (you can try going a bit further for availability if walking further is an option). Make sure to contact the host for the address before booking.
Eat
There are a few groceries carrying Kosher items, as well as two Kosher caterers. You can find more info on the Chabad website.
Explore
Now for that promised Shabbos excursion, Burlington’s charming streets won’t disappoint. Here are some of the most interesting destinations you might want to check out on your Shabbos afternoon walk. We also created this map with all stops on it. Think of this as your personal Shabbos walking tour. We included a short excerpt for each stop. If it interests you, click on the link to read more about it before visiting.
P.S. To cover all of them would include quite a lot of walking – much of it outside the eruv. So we recommend choosing your top spots and sticking to those. If you choose only one or two highlights, check out the Lake Champlain views and War of 1812 history at Battery Park and Waterfront Park.
- Ohavi Zedek Synagogue
Founded in 1885 by 18 Jewish immigrants from Lithuania, this is Vermont’s oldest synagogue. Originally Orthodox and now Conservative, it reflects the life of Eastern European Jewish immigrants in Burlington. - Old North End
Historic immigrant neighborhood where Jewish, Italian, and French Canadian families settled in the late 19th and early 20th centuries. Many Jewish shopkeepers and peddlers lived here. - Fletcher Free Library
Opened in 1886, this library is a Gilded Age civic project and one of Vermont’s largest public libraries. It represents a commitment to education, including for immigrant communities. - City Hall Park
A public green space in front of Burlington City Hall, historically a site for rallies, markets, and gatherings. Highlights Burlington’s abolitionist history and immigrant commerce. - The Flynn Theater
Opened in 1930 in Art Deco style, this theater hosted vaudeville and films. Many Jewish performers and cultural figures contributed to Burlington’s entertainment scene. - Farmer’s Market
Founded in the 1970s as a food-buying club, it reflects Burlington’s farm-to-table and natural foods movement. Today it remains a community hub. - Follett House
An 1820s mansion associated with rail and lake commerce wealth. Reflects Burlington’s rise as a commercial and industrial center. - Battery Park
Site of War of 1812 cannons and later a public park. Offers panoramic views of Lake Champlain and the Adirondack Mountains, blending military and civic history. - Lake Champlain Waterfront Park
Once industrial, now a revitalized park and trail system. Perfect for strolling, enjoying scenic views, and reflecting on Burlington’s relationship with the lake. - Wells-Richardson Building
Constructed in 1895, it housed the Wells-Richardson Company, known for patent medicines like Paine’s Celery Compound. A key example of late 19th-century commercial architecture. - Church Street Marketplace
A pedestrian-only street in the downtown core with 19th-century architecture. Historically a commercial hub, it’s now Burlington’s vibrant shopping and cultural area.
In the Area
There are many things to do in the area to fill up more than 4 days Chol Hamoed. Below is a list of some of the highlights:
- Vermont Teddy Bear
An adorable teddy bear factory where you can see how their made, design your own and even take home a new friend! - ECHO Vermont
The ECHO, Leahy Center for Lake Champlain is a fun interactive science and nature museum with interactive exhibits, live species and a 3D theater. - Shelburne Farms
A working farm on a mission to educate and share the wonders of the land. Enjoy their trails, specialty tours, or the children’s farmyard. - Shelburne Museum
Explore and discover art, history, and the natural beauty of Vermont at Shelburne Museum, an eclectic collection of over 100,000 pieces of art and history. From a full-sized old steam ship, to a working black smith, to modern art, it has something for everyone. - Boating
Enjoy a ride on Lake Champlain and enjoy the views. - Smugglers Notch Scenic Highway
Just look at the pictures. Need I say more? - Stowe, VT
About 40 min from Burlington, Stowe is an adventure lover’s haven – especially in the fall. Hike, bike, zipline, take a gondola, or enjoy the foliage in one of the many ways Stowe knows how to.
San Francisco, CA
Surrounded by elegant historic streets, sweeping city views, and the clang of cable cars climbing steep streets, a Shabbos in San Francisco gives you a chance to dive deeper into its history and cultural charm. The extra few days allow you time to fly in and out and enjoy all aspects of the city without needing much more.
Sukkah & Meals
Chabad has a publicly accessible sukkah at 873 Sutter Street, SF, CA. They also have day and night meals on Shabbos that can be reserved on their website.
Eat
There are a few Kosher restaurants in the area – and a few more in Oakland. Chabad has a comprehensive list of all Kosher options available. They will also be hosting a special BBQ Thursday night (October 9, 2025) in front of 423 10th Ave, SF, CA.
Stay
There are many hotel options within walking distance of Chabad. Following are a few:
- Hotel Adagio, Autograph Collection
- Hotel Nikko San Francisco
- Hotel Zepelin
- Cathedral Hill Hotel
- Axiom Hotel
- Found Hotel Carlton
- Hotel zetta
- Hampton Inn
- Petite Auberge
- Nob Hill Inn
- Ritz Carlton
- As well as some Airbnb options. Make sure to double check the location before booking.
Explore
Now for that promised exploration of history and culture – below we created a list of interesting destinations and areas to walk through. Make sure to drink plenty of water before leaving and enjoy the laid back stroll through San Francisco’s charming streets.
- Union Square
San Francisco’s premier public plaza, surrounded by historic buildings, fountains, sculptures, and open-air seating. A hub for shopping, people-watching, and cultural events. - California Street Cable Car
A historic cable car line dating back to the 1870s, running up and down San Francisco’s steep hills. Watching the cable cars is a quintessential city experience, showcasing early engineering ingenuity. - Nob Hill Architecture Walk
A stroll past grand hotels like the Fairmont and Mark Hopkins, plus restored Victorian mansions. The area reflects San Francisco’s Gilded Age wealth and offers stunning city and bay views. - Huntington Park
A small urban oasis with fountains, statues, and benches, located in front of the Fairmont Hotel. Perfect for a quiet pause amid the city’s hustle and bustle. - Dragon Gate / Chinatown
The iconic entrance to one of the oldest Chinatowns in the U.S., featuring pagoda-style architecture, murals, and lanterns. Window-shopping and strolling reveal the neighborhood’s vibrant cultural heritage. - Belden Place Alley
A narrow, charming European-style alley lined with historic buildings. Known for its intimate atmosphere, it offers a glimpse of San Francisco’s hidden urban character. - Fisherman’s Wharf
A little farther away (40 minute walk from Sutter St) is the famed Fisherman’s Wharf – a tourist favorite – with a colony of sea lions, shops and art galleries, street performances and the historic WWII submarine—the USS Pampanito, and more.
In the Area
Fill your 4 days of Chol Hamoed with everything else that San Francisco has to offer.
- Alcatraz Island
Alcatraz Island was once the most secure federal prison in the U.S., and held notorious inmates like Al Capone. After being decommissioned in 1963, the prison is now a museum, welcoming millions of curious travelers every year. Take a ferry and join a guided tour or explore at your own pace. - Golden Gate Bridge
What is a visit to San Francisco without an iconic picture at the Golden Gate Bridge? It really is beautiful. You can bike, walk or just enjoy the views from below. - Cable Cars
Take the chance to ride a classic cable car up the steep streets of San Francisco - Walt Disney Family Museum
Find animation, innovation, inspiration and immerse yourself in the remarkable life story of Walt Disney—the man who raised animation to an art, tirelessly pursued innovation, and created a distinctly American legacy. - Muir Woods
Just outside of San Francisco lie the impressive Muir Woods whose coastal redwood preserve features majestic redwoods and scenic hiking trails that draw more than 1.5 million visitors each year.
Savannah, GA
Savannah, is famous for its moss-draped oak trees, cobblestone streets, and beautifully preserved historic squares. Blending Southern charm with a vibrant cultural scene, Savannah feels like stepping into a storybook where history and modern life meet. It’s walkable streets and historic charm make this a perfect Shabbos destination.
Sukkah & Meals
Chabad offers meals and a publicly accessible Sukkah at 2424 Drayton Street. Contact them through their website to learn more.
Eat
Kosher food in Savannah is limited. There are Kosher aisles in two groceries and a catering service. Additionally, on Sunday October 12, Chabad will be hosting a Sushi in the Sukkah event for locals. You can contact [email protected] to see if joining is an option.
Stay
Many hotels are already sold out for the dates of Chol Hamoed. Only the following boutique hotels were still available when we checked.
- Bellwether House
- Forsyth Park Inn
- Amethyst Garden
- Azalae Inn
- Some nice Airbnb options were available as well. Double check with the host what the actual location is to make sure it is walking distance of Chabad.
Explore
Savannah is a beautiful city with moss covered trees and 22 squares dotting its streets. It has a rich history as Georgia’s oldest city and played key roles in the Revolutionary and Civil war. It is also home to the third oldest Jewish community in the US with the Shul Mickve Israel still standing, but it is sadly a reform temple nowadays.
Some of the points of interest you might enjoy on a stroll through the city are listed below. We also create this map which highlights them in order. Note: It is a lot to cover in one walking tour. We recommend you start at Forsyth Park (20 min from Chabad) and make your way through some of the squares heading towards the Riverfront. City Market is also really nice if you like vibrant city squares.
Savannah is also really big on haunted history, so if that’s your thing, do a little more research and make some of these items a highlight. And of course if you’d like to add more cultural stops or historical stops to your walk – there’s plenty of that as well.
Many of the historical houses (the ones listed below and many not listed as well) offer guided tours. If any of these spots look interesting – make sure to return Sunday for a guided tour before heading home.
- Forsyth Park
The city’s grand 30-acre park, established in the 1840s, a hub of local life and historic monuments. Following are some of its highlights.- Garden of Fragrance (Whitaker Street side) – A sensory garden designed for the visually impaired, filled with aromatic blooms.
- Spanish Moss & Live Oaks – Iconic trees draped in Spanish moss create Savannah’s most photographed canopy.
- Civil War Monument (Center of Park) – Erected in 1870s to honor Confederate soldiers, one of many Civil War memorials in Savannah.
- Fountain (North End of Park) – Installed in 1858, this striking fountain was modeled after Parisian designs and is Savannah’s postcard symbol.
- Monterey Square – Built in 1847, widely considered the most beautiful of Savannah’s squares with a monument honoring Revolutionary War hero Count Casimir Pulaski, mortally wounded in Savannah in 1779.
- Taylor Square (formerly Calhoun Square) – The last of Savannah’s historic squares, surrounded by preserved 19th-century homes.
- Mercer Williams House Museum – Famous from Midnight in the Garden of Good and Evil, this 1860s mansion blends beauty and mystery.
- The Old Sorrel Weed House Museum – One of Savannah’s most haunted homes, with Greek Revival and Regency architecture.
- Flannery O’Connor Childhood Home – The writer’s childhood house, showcasing her life and Southern Gothic legacy.
- Madison Square – Site of the 1779 Revolutionary War battle; now ringed by historic architecture.
- Historic Savannah Theatre – America’s oldest continually operating theatre, dating back to 1818.
- Chippewa Square – Famous for the Forrest Gump bench scene, named for the Battle of Chippewa in 1812.
- Owens-Thomas House & Slave Quarters – A Regency-style mansion (1819) with preserved slave quarters offering powerful history.
- Johnson Square – The first and largest square, laid out in 1733; burial place of General Nathanael Greene.
- Wright Square – One of the original 1733 squares, site of Tomochichi’s grave, the Yamacraw chief who welcomed Oglethorpe – the founder of Savannah.
- Reynolds Square – Features a statue of John Wesley, founder of Methodism, who preached in Savannah.
- The Olde Pink House – Built in 1771, this mansion-turned-restaurant survived fire and war, now a Savannah dining landmark.
- Davenport House Museum – 1820 Federal-style home that launched Savannah’s preservation movement.
- Telfair Academy – Opened in 1886, the South’s first public art museum, housed in a neoclassical mansion.
- Harper Fowlkes House – A Greek Revival gem (1842) with lavish interiors and history tied to local elites.
- City Market – A historic commercial hub rebuilt after fires and hurricanes; today a cool lively pedestrian market with arts, dining, and shopping.
- The Pirates’ House – Established in 1753, once a tavern for seafarers and (legendary) pirates, now a family restaurant.
- The Waving Girl Statue – Honors Florence Martus, who greeted ships for 44 years with a wave and lantern.
- Emmet Park – A riverside green named for Irish patriot Robert Emmet, with memorials to Savannah’s Irish community.
- Factor’s Walk – Historic cotton warehouses and cobblestone lanes once at the heart of Savannah’s cotton trade.
- Riverfront – Former cotton export hub, now a bustling strip of shops, cafes, and views of ships on the Savannah River.
In the Area
There is truly something for everyone in Savannah. Some highlights include:
- River cruises – Enjoy sightseeing cruises, sunset cruises or dolphin watching cruises
- Museums – History, prohibition, art, railroads, maritime, writers – whatever your interest, there’s a museum for you.
- Tours – Whether you want to learn more about the city, enjoy a pub crawl, or get scared on a haunted tour – you can find a tour that suits your needs.
- Fort Pulaski National Monument – Fort Pulaski is a Civil War-era fortress where visitors can explore massive brick walls, dry moats, and restored casemates with historic cannons. Its scenic river and marsh views make it a striking blend of history and natural beauty.
- Tybee Island – Tybee Island is Savannah’s breezy escape, where salty air and gentle waves create an easygoing coastal rhythm. Pastel cottages, a towering lighthouse, and golden sunsets give it the feel of a timeless seaside retreat, perfect for slowing down and soaking in the view. Perfect to spend the day or make a day trip of it. Easily accessible by car (or uber) via bridge.
The following cities also make great locations to explore over Shabbos – since there are already plenty articles on them, we’ll just link these below.
- Boston, MA
- Philadelphia, PA
- Washington DC
- Newport Rhode Island
Please let us know in the comments if you visit any of these places and how your experience is.
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