Rutland

Day Trips

Make the most of your day with our curated plans, packed with Rutland's hidden gems and unique experiences!

day 1
Welcome to Rutland
morning
:

Begin your journey in Rutland with a hearty breakfast at a local diner. Afterward, take a leisurely stroll around the picturesque downtown area, admiring the historic architecture and unique shops. Don’t forget to grab some coffee to fuel your day ahead.

afternoon
:

Visit the Rutland County Museum to dive into the rich history of the area and learn about its culture. Enjoy lunch at a cozy café before heading to the beautiful Pico Mountain for some outdoor adventure. Spend the afternoon skiing, snowboarding, or hiking, depending on the season.

evening
:

Enjoy a relaxing dinner at one of the restaurants downtown that serves farm-to-table dishes. After dinner, catch a local theater performance or live music event that highlights the talent of Rutland residents. Wind down your day with a nightcap at a nearby pub.

day 2
Explore the Green Mountains
morning
:

Start your day with breakfast at a scenic spot along the Green Mountains. Lace-up your hiking boots for an invigorating trek on one of the beautiful trails where you can choose between easy strolls or challenging hikes. Encounter stunning views and the tranquil sounds of nature.

afternoon
:

Once you reach the summit, enjoy a packed lunch while soaking in the panoramic vistas. Spend the early afternoon exploring the surrounding area or return downhill for a visit to one of the local farms. Engage with locals and learn about their farming practices and seasonal produce.

evening
:

Treat yourself to a delightful dinner at a rustic lodge that highlights local ingredients cooked to perfection. Afterward, reflect on your day by visiting a local brewery where you can sample craft beers made in the area. Enjoy the relaxed atmosphere and make new friends with fellow travelers.

day 3
Cultural Day
morning
:

Kick off your cultural immersion with breakfast at a historic inn that reflects Rutland's past. Then, delve into the city's arts scene by visiting local galleries showcasing works from regional artists. Spend some time at the Paramount Theatre, even if just to appreciate its architectural beauty.

afternoon
:

After lunch at a quaint bistro, embark on a self-guided tour of the public art installations around town. Engage with the diverse storytelling found in murals and sculptures that depict the essence of Rutland. Consider checking out a craft workshop for a hands-on creative session.

evening
:

End your day with a culinary experience at a fine dining restaurant, where you can savor exquisite dishes paired with local wines. Attend an evening poetry reading or an art exhibition opening that enhances your cultural experience. Come back to your accommodation inspired and enriched by the local arts scene.

day 4
Nature Adventure
morning
:

Wake up early to witness the sunrise over the lakes while enjoying breakfast outdoors. Revel in the serene beauty as birds chirp and the world around you comes to life. Pack your gear for a day filled with fishing or kayaking.

afternoon
:

Spend the afternoon at Lake Bomoseen, where you can fish in tranquil waters or paddle through scenic routes. Have a picnic lunch by the shore and relish the extraordinary landscape all around you. Consider a swim if the weather permits to cool off and refresh.

evening
:

Dine at a lakeside tavern that offers fresh Catch-of-the-Day dishes. As the sun sets, take a peaceful boat ride to witness the vibrant colors reflecting on the water. Conclude your evening with stargazing as the clear Rutland skies unveil a blanket of stars.

day 5
Farm Tour Day
morning
:

Start your day with visits to local farms where you can indulge in a hearty farm breakfast featuring fresh, local produce. Learn about the farming process and meet some of the locals who contribute to Rutland’s agricultural scene. This experience provides a deeper connection to the land.

afternoon
:

Take a guided tour of nearby farms that offer a range of activities like berry picking or cheese tasting. Relish lunch with a farm-fresh salad, and engage in picking your own fruits or vegetables if in season. This hands-on experience gives you insight into the rural life of Vermont.

evening
:

Enjoy a farm-to-table dinner prepared by renowned chefs that highlight the bounty of local farms. Engage with farm owners and local chefs, sharing stories and experiences of the day's labor. Wrap up your evening with a cozy bonfire, enjoying s'mores under the starlit sky.

day 6
Adventure Sports Day
morning
:

Fuel up for a day of adrenaline by having an energizing breakfast smoothie at a café focused on healthy eating. Choose an adventure sport to dive into, such as mountain biking on expert trails or zip-lining through the trees. The thrill will set the tone for an active day.

afternoon
:

Spend your afternoon engaged in your chosen activity, challenging yourself and experiencing the heart-pounding excitement of adventure. After a morning of exhilaration, relax with a hearty lunch at a nearby food truck serving up delicious bites. Reflect on your shared experience with fellow thrill-seekers.

evening
:

As the sun sets, grab dinner at a local bar that boasts an inviting convivial atmosphere. Participate in trivia night or a fun game session, continuing the excitement of your adventurous day. Gather stories to share with friends and enjoy the lively energy around you.

day 7
Historical Exploration
morning
:

Begin your historical exploration with breakfast at a café housed in a repurposed historic building. Visit the local historical society or take a guided walking tour of the downtown area, where you'll learn about the legacy of Rutland and its notable figures. Engage with stories that shaped this charming town.

afternoon
:

After lunch, explore the historic Civil War-era sites and old churches that breathe life into Rutland's past. Don't miss out on the chance to stop by the unique shops along the way and perhaps pick up a historical memory to take home. Be sure to capture photographs of the quaint, historical architecture.

evening
:

Find an inviting place to dine that features local flavors, often with historical significance in its recipes or menu. Join a local ghost tour in the evening to hear tales of Rutland's haunting past while exploring the city once more under the moonlight. End your evening reminiscing about the history that surrounds you.

day 8
Relaxing Day at the Spa
morning
:

Indulge in a luxurious spa breakfast that will set the stage for a day of relaxation. Enjoy some time at a local wellness center, where you can start your day with meditation or yoga amidst beautiful scenery. A calm, centered morning will help prepare you for pampering.

afternoon
:

Treat yourself to a variety of spa treatments, whether it’s massages, facials, or hydrotherapy sessions. Enjoy a light lunch at the spa’s café featuring health-conscious options that nourish the body and spirit. Spend the afternoon unwinding in relaxation lounges or enjoying a soak in calming pools.

evening
:

Conclude your spa day with a dining experience at an upscale restaurant focusing on healthy, gourmet food. Engage in meaningful conversations with the friends you brought along or with other guests you’ve met. Leave feeling rejuvenated and ready to embrace the remaining days of your Rutland adventure.

day 9
Local Market Discovery
morning
:

Start your final day with breakfast at a popular local bakery known for its fresh pastries. Visit the Rutland Farmers Market, where you'll find fresh produce, handmade goods, and the vibrant spirit of the community. Engage with local farmers and artisans about their crafts and produce.

afternoon
:

After a leisurely market stroll and tasting treats, join a cooking class that focuses on using seasonal local ingredients. Collaborate with fellow participants to create delicious dishes that reflect Rutland’s culinary diversity. Enjoy your prepared meal together and exchange tips about local cuisine.

evening
:

Enjoy a farewell dinner at a charming restaurant that features a menu celebrating local flavors. Reflect on your Rutland experience while enjoying the ambiance and flavors of the meal. Close your journey with a toast to new memories and friendships developed during your adventure.

Discover Rutland

Read more in our Rutland 2025 Travel Guide.

Rutland Travel Guide