Oakland Travel Guide

Explore the natural and cultural attractions of Oakland in Maine. Get insider tips on local food and drink, accommodations, transportation options, safety and health, and nearby destinations.


Introduction to Oakland

Oakland is a vibrant town nestled in the heart of Maine’s Lakes and Mountains region. Located in Oxford County, Oakland offers a perfect mix of natural and cultural attractions, making it a popular destination for visitors. It’s a great place to explore the outdoors, hunt, bike, hike, and fish. There are also many historical sites, museums, and art galleries in Oakland, which provide insights into the town’s rich cultural and economic history.

List of Places to Visit in Oakland

Whether you’re an adventure-seeker, history buff, foodie, or culture lover, there’s something for everyone in Oakland. Here’s a list of must-visit places:

Culturally Important Attractions: Museums and Historical Places

  • The Belgrade Historical Society Museum: This museum offers visitors an opportunity to explore the rich history of Oakland and the surrounding area. It’s a perfect place to learn about the pioneer days, early industry, and contributions of the town to the state and the nation.
  • The Messalonskee Historical Society: Exhibits at the Messalonskee Historical Society Museum cover the town’s rich heritage and are located in the historic Benjamin Berry House.
  • The Colby College Museum of Art: Located just outside of Oakland proper, the Colby College Museum of Art displays a vast collection of American art from the 18th century to the contemporary period. It’s a must-visit place for art enthusiasts.

Natural Attractions in Oakland: Outdoor Adventures and Scenic Views

  • Messalonskee Lake: Messalonskee Lake is a significant landmark in Oakland and is an ideal spot for a picnic, swimming, and boating. The park contains an abundance of walking trails, bridges, and picnic areas. The lake is a paradise for water sports enthusiasts.

  • Kennebec Highlands: This conservation area offers 6,000 acres of woodland, marsh, and waterways for outdoor enthusiasts to explore. It is perfect for hiking, birding, and fishing in Sebasticook Lake.

Hiking/Biking Routes of Oakland

  • Belgrade-Bristol Legacy Trail: This 7.7-mile trail is perfect for bikers and hikers, offering stunning views of Messalonskee Lake.

Best Things to Do in Oakland: Activities and Tours

  • The Oakland Kayak Tour: This tour offers visitors an opportunity to explore the beauty of Messalonskee Lake up close. Kayaks, paddling equipment, and life jackets are provided.

Week-Long Itinerary for Oakland

Day Activity Description
Day 1 Colby College Museum of Art Explore the vast collection of American art from the 18th century to the contemporary period.
Day 2 Belgrade-Bristol Legacy Trail Enjoy a scenic biking or hiking on this 7.7-mile trail.
Day 3 Messalonskee Lake Picnic, swim or boat on this beautiful lake.
Day 4 Belgrade Historical Society Museum Learn about Oakland and the surrounding area’s rich history.
Day 5 Oakland Kayak Tour Spend the day kayak through the pristine beauty of Messalonskee Lake.
Day 6 Kennebec Highlands Spend the day exploring the 6,000 acres of woodland, marsh, and waterways for outdoor enthusiasts to explore.
Day 7 Soaring Eagle Lodge & Campground Relax and enjoy oak-lined waterfront RV sites at Soaring Eagle Lodge & Campground

Food and Drink Scene of Oakland

When it comes to food and drink in Oakland, there are plenty of options to choose from. Here are some must-try dishes and local beverages:

Must-Try Dishes

  • Lobster: No trip to Maine is complete without trying fresh lobster. Find it in local restaurants, seafood shacks, and markets.
  • Whoopie Pie: This sweet, fluffy dessert is a state specialty, with many local bakeries selling their versions.

Local Beverages

  • Allen’s Coffee Brandy: Allen’s Coffee Brandy is Maine’s favorite liqueur, and it can be enjoyed on its own, over ice, or mixed in with hot coffee.

Where to Stay in Oakland: Hotels, Hostels, and Guesthouses

Oakland provides a range of accommodation options suitable for all budgets. Here are some options:

  • Campgrounds: Soaring Eagle Lodge & Campground
  • Hotels: Hampton Inn, Oakland House Seaside Resort

What to Buy in Oakland: Souvenirs and Local Products to Bring Home

Visitors can take home memories of Oakland in the form of locally made maple products, pottery, jewelry, and crafts. Oakland’s local farmers’ markets are also popular places to purchase fresh locally grown food products.

Local Culture and Customs of Oakland

Oakland has a rich history and a deep sense of community. The town’s residents are friendly and welcoming, and visitors will often find themselves engaging in conversations with locals.

Best Time to Visit Oakland

The best time to visit Oakland is during the summer months between June and August, when the weather is ideal for exploring outdoors. Fall is also a great time to visit, with warm days and cool evenings ideal for hiking or viewing fall foliage.

Do’s and Don’ts of Oakland

Do:

  • Respect local customs and traditions, especially when it comes to tipping as it may vary from usual.
  • Take some time to talk to the locals and learn about the town’s history.

Don’t:

  • Litter- Maine is known for its pristine wilderness, so please maintain cleanliness.
  • Take things without permission - Trespassing is illegal, so obtain permission from the property owner before visiting.

Safety and Health

Safety in Oakland

Oakland is a safe and welcoming town, and it maintains low crime levels. It is a quiet town, and visitors should always take basic precautions, such as locking their cars and being aware of their surroundings, especially at night.

Health in Oakland

There are several hospitals, medical centers, and clinics near Oakland in case of a medical emergency.

Getting to Oakland: Transportation Options and Logistics

Visitors traveling to Oakland have an array of transportation options available. Here are a few:

Airports Near Oakland

  • Portland International Jetport: Located about one hour and forty minutes south of Oakland, this the best option when flying in from other parts of the country or internationally.

Bus Stations Near Oakland

  • Concord Trailways provides daily bus service to Oakland.

Other Options

  • Visitors can also opt to drive or rent a car to reach Oakland.

How to Get Around in Oakland

Renting a car is the best way to get around Oakland. There are also taxi cab services and bikes available for rent. Visitors can walk around the town as it isn’t huge, making it easily accessible.

Where to Go Next from Oakland: Nearby Destinations and Excursions

There are plenty of exciting nearby destinations and excursions from Oakland, including:

  • Augusta: This charming town is home to the Maine State Museum, the All-American Speedway, and several parks and historic sites.

  • Portland: Portland’s Old Port Historic District or the Portland Museum of Art, are famous for its outlet malls.

Conclusion

Oakland is a town that offers a great mix of natural beauty and cultural attractions. With friendly locals, a rich history, and opportunities to relax or go on an adventure, it’s an ideal place to visit. From museums to lakes, hiking trails to amazing food, there’s something for everyone in Oakland.

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