After a day of exploration, what better way to relax than in a charming downtown full of activities, dining, and entertainment? These vibrant urban areas serve as the perfect basecamp for adventure, offering something fun for the whole family while keeping you close to the great outdoors. From intriguing museums and scenic trails to cozy cafes and local gear shops, kick off your new year with this guide to some of the best downtowns and Main Streets in our region!
A Shenandoah Valley Escape in Staunton, VA
Nestled in the heart of the Shenandoah Valley, downtown Staunton is a charming, walkable hub that spans five lively square blocks. With its blend of independent retailers, award-winning restaurants, and cultural landmarks, Staunton’s downtown offers something for everyone. The city’s rich history shines through its beautifully preserved architecture and multiple historic districts, making it a perfect destination for exploration, dining, and shopping.
Nearby Outdoor Adventures
Just minutes from Staunton’s lively downtown, outdoor enthusiasts can immerse themselves in a variety of natural escapes. Local parks such as Gypsy Hill, Montgomery Hall, and Betsy Bell & Mary Gray Wilderness offer tranquil walking trails and stunning scenic overlooks. For a more adventurous experience, Shenandoah National Park and George Washington National Forest are just a 30-minute drive away, featuring over 500 miles of hiking trails, including iconic routes like Old Rag and Hawksbill.
For even more adventure, book a trip with Vivid Earth Adventures, offering thrilling activities like climbing, rappelling, and canoeing.
In Town To-Dos
Downtown Staunton is a lively hub with unique retailers, top-notch restaurants, and cultural attractions. Shop for one-of-a-kind items at Latitudes Fair Trade Store, Made; By the People, For the People, and Wilderness Adventure. For a meal, visit Sweet Addie’s Waffle Shop, Cranberry’s Grocery & Eatery, Zynodoa, or The Depot Grille, all offering locally inspired cuisine. End your day with a craft brew at Redbeard Brewing Company, a local favorite.
Cultural experiences abound with the American Shakespeare Center, the Woodrow Wilson Presidential Library & Museum, and the Camera Heritage Museum. Don’t miss the Historic Downtown Staunton Walking Tour, which highlights Victorian architecture and landmarks like Trinity Episcopal Church’s Tiffany stained-glass windows. For local produce and crafts, visit the Staunton Farmer’s Market, happening from April until December.
With its ideal location, Staunton serves as the perfect basecamp, blending easy access to world-class outdoor adventures with the convenience and charm of its downtown amenities.
Downtown Events
- Queen City Mischief & Magic Festival
Each fall, downtown Staunton transforms into a magical realm with wizard-themed activities. - Staunton Music Festival
Held every August, this multi-day event brings world-class musicians to stunning venues downtown.
Experience the NEW Cumberland in Allegany County, MD
Nestled in the heart of Allegany County, the Mountain Side of Maryland, Cumberland, MD, serves as the county seat. With a downtown area spanning approximately 21 acres, it offers a compact yet vibrant hub for both residents and visitors to explore.
A Top Adventure Downtown
Cumberland has been recognized by BRO as a Top Adventure Town with its connectivity to many outdoor recreation opportunities. It is also a Trail Town, as the downtown is just steps from the internationally recognized Great Allegheny Passage, a 150-mile trail system connecting Cumberland to downtown Pittsburgh. The trail connects to the C&O Canal, offering cyclists a 334-mile route from Pittsburgh to Washington, DC. The C&O Canal is one of the most-visited national parks in the country and the most visited in Maryland!
The Potomac River is also iconic to downtown Cumberland as it forms the entire southern border of Allegany County and has earned a position as one of the region’s major drivers of tourism. Visitors come with inner tubes, canoes and kayaks to enjoy the water’s mild rapids. For those who don’t have their own vessels, there are plenty of outfitters available. Outside of city limits but yet a short drive away is access to 70,000 acres of public land in state parks and a forest, as well as ample opportunities for hiking, backpacking, rock climbing, and more.
Must-Visit Spots
Cumberland’s downtown combines history, outdoor adventure, and local flavor, with the Allegany Museum, outdoor outfitters like Wheelzup Adventures, local coffee at Basecamp, craft beer at Dig Deep Brewing, and classic eats from Queen City Creamery Scoop Shop and Curtis’ Coney Island Famous Weiners.
In addition to these businesses, Cumberland offers notable sites and tours for those looking to explore its history and culture. Emmanuel Episcopal Church, is a historic site that also served as a station on the Underground Railroad. The Cumberland Arts & Entertainment District showcases galleries, performance spaces, and cultural events, supporting local artists and entrepreneurs while enhancing the city’s vibrant arts scene.
A New Look!
Cumberland revealed its revitalized historic downtown in November 2024, completing a decade-long redevelopment that modernized infrastructure, added new businesses, and breathed new life into this vibrant hub for visitors and residents alike.
Step into a Vibrant Downtown in Salem, VA
The charming City of Salem, Virginia, is perfectly situated for a mountain getaway, conveniently accessible via State Route 460 and I-81. In Salem, the heart of dining, nightlife, and entertainment lies in its vibrant historic downtown.
Adventure is All Around
Downtown Salem is the perfect hub for outdoor adventures. Within minutes you can find yourself on world-class mountain bike trails and epic hiking trails, including the most famous footpath on the East Coast — the Appalachian Trail. On weekends between March and November, the innovative McAfee Knob Shuttle takes hikers from downtown Salem directly to the trailhead.
For paddlers and anglers, the Upper James River Water Trail and the Roanoke River Blueway are nearby. Both rivers offer great scenery and relaxing tubing trips.
A Lively Main Street
Salem is not your typical sleepy, small town Main Street. Downtown Salem is alive with shops, restaurants, craft beer, a farmers market and vibrancy inspired by the campus of Roanoke College. You’ll want to stay a few days to take in the sites and the outdoor recreation. Boutique lodging in downtown makes it easy to walk to shops and restaurants. The Rowland Hotel is home to the upscale Frankie Rowlands Steakhouse. A few blocks away, The Lofts at Downtown Salem offers stylish one-bedroom loft style accommodations in a restored 1924 building that once housed an automobile dealership.
Known as Virginia’s Championship City, sports fans can plan a visit to catch some action. Salem hosts college championships and other sports tournaments throughout the year. Every spring and summer, the Salem Red Sox play home games in one of the most scenic minor league stadiums in America. For two weeks each summer, the Salem Fair rolls into town with rides, games, music and food.
Downtown Events
- Olde Salem Days – Join the City of Salem and Rotary Club on September 13th to celebrate locally handmade, hand-altered, and home-baked crafts!
- Lewis Gale Salem Half Marathon – Experience the charm of downtown Salem on the run! Sign up now for races of varying distances, happening October 11th.
Experience the Heart of Harford in Bel Air, MD
Set in the heart of Harford County, Maryland, just 30 minutes north of Baltimore, the Town of Bel Air is a radiant community celebrated for its historic charm and welcoming atmosphere. This picturesque town boasts tree-lined sidewalks and an array of independently owned shops and restaurants.
Tours and More!
Explore the 2-mile self-guided Public Art Tour, showcasing 25 pieces of public art, with 15 additional works nearby. Or take the Historic Walking Tour to admire 19th and 20th-century architecture, and visit landmarks like the County Courthouse and the restored Bel Air Armory, a hub for community events. Unique shops such as REB Records, Twisted Roots Rare and Common Plants, and the Nest on Main, along with dining options like Vagabond Sandwich Company and One-Eleven Main, make the town a destination for all.
Parks and Trails to Explore
Outdoor enthusiasts will find plenty to explore in Bel Air, starting with the scenic 4.5-mile MA & PA Heritage Trail, which winds through beautiful landscapes and offers a peaceful escape for walkers, runners, and cyclists. Pick up the trail at the centrally located Williams Street Trailhead, conveniently situated near Independent Brewing Company, where you can reward yourself with a refreshing local brew after your adventure. For even more outdoor experiences, head to Rocks State Park to hike to the iconic King and Queen Seat, a breathtaking overlook, or explore the lush trails, waterfalls, and riverfront views at Susquehanna State Park.
As a designated Main Street Maryland Community and Arts & Entertainment District, Bel Air brings energy and charm to every season with a calendar full of festivals, events, and cultural celebrations. From art shows and concerts to holiday markets and community gatherings, there’s always something happening to entertain visitors of all ages and interests. Whether you’re seeking outdoor thrills, local flavor, or artistic inspiration, Bel Air offers a little something for everyone.
Downtown Events
- The Chocolate, Brew & Wine Tour – March 1: Enjoy a pub crawl with drinks, sweet treats, and exclusive offers. Tickets sell out fast, so grab yours now for a fun day of beer and chocolate!
- Annual Kite Festival–April 12: Enjoy a day of kite flying, live music, and food for the whole family! Free kites (while supplies last) and help for beginners are available. 10AM–4 PM, free admission.
Explore the Capital of Bourbon Country in Frankfort, KY
Plan your next adventure in Kentucky’s capital city, where downtown Frankfort offers a perfect mix of history, culture, and scenic beauty. Spanning a compact, walkable area of four by six blocks, this inviting destination is ideal for a leisurely day of exploration.
Easy Access to Adventure
Nestled alongside the picturesque Kentucky River, downtown Frankfort provides easy access to outdoor activities with three river entry points. Visitors can enjoy paddling rentals, embark on guided riverboat tours, or simply take in the serene views from the water’s edge.
Downtown Frankfort offers a variety of engaging tours that highlight the city’s rich history, scenery, and vibrant culture. The Bourbon Blazer tour takes visitors on a spirited journey through Frankfort’s bourbon heritage, blending tastings with stories of Kentucky’s famous distilleries. For those seeking a broader experience, additional guided tours showcase Frankfort’s historic landmarks, architectural gems, local art, and unique charm.
Savor, Shop and Discover Downtown
Downtown Frankfort invites you to indulge in a culinary adventure with an array of local dining options. Whether you’re in the mood for upscale Southern cuisine at Serafini or a more casual vibe at Bourbon on Main, the downtown food scene offers something for every palate. Pair your meal with Kentucky-crafted bourbon or explore cozy cafés and bakeries, like Andy’s Artisan Bread or Engine House Coffee, for a sweet treat or quick pick-me-up.
Immerse yourself in Frankfort’s history and culture by visiting the Capital City Museum, where exhibits share stories of the city’s bourbon legacy and political past. Afterward, enjoy a stroll through downtown’s unique shops, like Completely Kentucky, featuring handcrafted goods by local artisans, or Glitterati Treasures, a favorite for jewelry and fashion lovers.
Whether you’re indulging in local flavors, uncovering history, or paddling the Kentucky River, downtown Frankfort promises a fun and enriching escape.
Downtown Events
- Downtown Derby Celebration Kick off Derby season in Downtown Frankfort on May 3, 2025, with live music, a delicious breakfast, signature cocktails, family-friendly activities, and community races!
- Bourbon on the Banks Festival Occurring October 4, 2025 along the Kentucky River, features bourbon tastings, live music, artisan goods, and more, with 60+ distilleries, breweries, and wineries.
Downtown Delights in Lexington, Buena Vista, and Rockbridge County, VA
Located in the southern Shenandoah Valley near the Blue Ridge Mountains, Lexington and Buena Vista in Rockbridge County offer walkable downtowns with free parking and plenty to explore. Lexington’s historic Main Street and Buena Vista’s Magnolia and Beech Avenues are hubs for shopping and dining, enriched by the energy of nearby colleges—Washington and Lee University, Virginia Military Institute, and Southern Virginia University.
Nature Within Reach
Wood’s Creek Trail, a 2.25-mile path within Lexington, winds along Woods Creek and through wooded areas. It connects to the seven-mile Chessie Nature Trail, a rail-trail linking Lexington and Buena Vista along the Maury River, showcasing diverse wildlife and flora. Just a mile from downtown, Boxerwood Nature Center and Woodland Garden offers birdwatching, a children’s play area, and fairy woods.
Buena Vista, an Appalachian Trail Community and gateway to the Blue Ridge Parkway, features Glen Maury Park, a 315-acre recreational area with nearly nine miles of trails, kayak and bike rentals, camping, and summer concerts. In spring, it hosts Gravista, a gravel bike race with two challenging routes: Stoked 60 (68 miles, 8,524 feet climb) and Worthy 30 (34 miles, 4,400 feet climb).
Less than 15 miles from Lexington or Buena Vista, Natural Bridge State Park features the iconic 217-foot limestone arch, hiking trails, disc golf, and ranger-led stargazing as part of its International Dark Sky Park designation.
Tours and More!
The Lexington Carriage Company provides enchanting, narrated horse-drawn carriage tours through historic downtown Lexington, running from spring to fall and continuing into the festive Christmas season. History enthusiasts will appreciate cadet-led tours of Virginia Military Institute and the VMI Museum, along with visits to the Jackson House Museum, the only home ever owned by Thomas J. “Stonewall” Jackson. For a spookier experience, Haunting Tales, led by artist and entertainer Mark Cline, delve into Lexington’s ghostly lore.
Just five miles north of downtown, Hull’s Drive-In Theater—a 74-year-old local treasure—offers classic movies under the stars, live music, and a 0.25-mile walking and fitness trail, making it a perfect spot for a nostalgic evening out.
Visit RockbridgeOutdoors.com for hiking, cycling, paddling, and other outdoor experiences in Rockbridge County, VA.
Downtown Events
- The Freedom Food Festival, held annually on July 3rd, transforms Main Street into a festive hub with a chef-led cook-off and proceeds benefiting local nonprofits.
- On the first Friday of each month, art galleries host receptions with new exhibits, live music, and artist meet-and-greets.
- Every Friday, Purveyors on Main and Lexington Mercantile offer free wine tastings to kick off the weekend.
An Appalachian Basecamp in Tazewell, VA
Tazewell’s Main Street serves as the vibrant centerpiece of Tazewell, Virginia, surrounded by the stunning beauty of the Appalachian Mountains. This quaint downtown blends historic charm with modern conveniences, offering a lively destination for both locals and visitors. With its unique array of shops, restaurants, and accommodations, Main Street exudes a warm, welcoming energy that showcases the heart of this close-knit community.
Minutes Away from Exploration
Tazewell’s Main Street is perfectly situated just minutes from some of the region’s most breathtaking outdoor destinations, making it an excellent starting point for adventure. Explore Cavitt’s Creek Park & Lake Witten, where you can enjoy kayaking, fishing, birdwatching, or simply soaking in the peaceful surroundings. Nearby, Lincolnshire Lake and Park offers activities like hiking, fishing, kayaking, and paddleboarding, along with an aqua park for family fun.
For a truly unique experience, visit Burke’s Garden, affectionately known as “God’s Thumbprint.” This stunning valley is celebrated for its remarkable geological features and offers direct access to the Appalachian Trail, making it a must-visit for hiking enthusiasts and nature lovers.
Town Treasures and Tasty Treats
Tazewell’s Main Street is filled with unique businesses that enhance its charm. Explore Between Friends Gifts, a boutique featuring local artisan goods, seasonal décor, and one-of-a-kind treasures. Stop by The Happy Goat for artfully crafted sandwiches, soups, salads, and grab-and-go snacks, along with a selection of hiking gear. Don’t miss Bee Noodle’d, a popular spot known for its excellent food and lively events. For a truly memorable stay, book a night at The Old Jail, where historic architecture meets modern comfort.
In addition to its shops and dining, Main Street showcases its creative side with attractions like Art on Main. Colorful murals, including “Standing Tall and Proud: Tazewell County’s African American Heritage,” bring vibrant artistry to the downtown area. Whether you’re looking to shop, dine, or soak in local culture, Tazewell’s Main Street has something for everyone.
Downtown Events
- Main Street Merchants: Year-round festive events hosted by local merchants!
- Main Street Moments: A signature event showcasing the best of Tazewell’s Main Street.
- Oktobrewfest: A festive fall celebration with local brews, music, and activities.
Discover Winter Warmth and Outdoor Adventures in Front Royal, VA
Nestled in the heart of the Shenandoah Valley, Front Royal, VA, is the ultimate basecamp for winter exploration. Its charming downtown is just minutes from breathtaking trails, serene rivers, and the iconic Skyline Drive—an adventurer’s gateway to Shenandoah National Park.
Brisk Hikes and a Cozy Retreat
For those seeking outdoor thrills, embark on a brisk winter hike to Compton Peak, where dramatic rock formations and sweeping vistas reward your efforts, or take in the stunning panoramic views along the Buzzard Rock Trail, a local favorite for its ridge-top scenery. If you prefer a cozy retreat after your adventure, head to downtown Front Royal, where charming cafés, local eateries, and inviting shops offer the perfect places to warm up, relax, and enjoy a taste of the town’s hospitality. Whether you crave the crisp mountain air or a snug indoor escape, Front Royal has something for everyone this season.
When in Town
Savor delicious eats at On Cue Sports Bar & Grill, where hearty meals and a lively atmosphere make it a favorite gathering spot, or unwind with a locally brewed beer at Vibrissa Beer, known for its creative brews and welcoming vibe. Need a caffeine fix? Stop by Melania’s Gourmet for expertly handcrafted coffee, pastries, and a cozy place to recharge. Downtown’s local shops and businesses are brimming with unique finds, from artisan goods and handcrafted gifts to specialty products, all served with a warm smile.
For a dose of local history, visit the Warren Heritage Society, where exhibits and historic buildings tell the story of Front Royal’s rich past. Art lovers can head to the Blue Ridge Arts Council to explore inspiring exhibits that showcase the talent and creativity of regional artists.
This January, embrace both the outdoors and the warmth of small-town charm. Whether you’re here for a day or a weekend, Front Royal invites you to experience its perfect blend of adventure and coziness.
Downtown Events
Celebrate Earth Day and kick off Spring Front Royal style! Lone Pine Day is based on the iconic lone pine overlooking the town, and will connect you with diverse, nature-oriented conservation groups that showcase environmental stewardship at its best.
